SU1054346A1 - Process for preparing 5-dimethylamino-1-naphthalene-sulfochloride - Google Patents
Process for preparing 5-dimethylamino-1-naphthalene-sulfochloride Download PDFInfo
- Publication number
- SU1054346A1 SU1054346A1 SU823434737A SU3434737A SU1054346A1 SU 1054346 A1 SU1054346 A1 SU 1054346A1 SU 823434737 A SU823434737 A SU 823434737A SU 3434737 A SU3434737 A SU 3434737A SU 1054346 A1 SU1054346 A1 SU 1054346A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dimethylamino
- yield
- naphthalene
- acid
- sulfochloride
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- BBEQQKBWUHCIOU-UHFFFAOYSA-N 5-(dimethylamino)-1-naphthalenesulfonic acid(dansyl acid) Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(O)(=O)=O BBEQQKBWUHCIOU-UHFFFAOYSA-N 0.000 claims abstract description 5
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 7
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 description 8
- XPDXVDYUQZHFPV-UHFFFAOYSA-N Dansyl Chloride Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(Cl)(=O)=O XPDXVDYUQZHFPV-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
СПОСОБ ПОЛУЧЕНИЯ 5-ДИМЕТИЛАМИНО-1-НАФТАЛИНСУЛЬФОХЛОРИДА на основе 5-диметиламино-1-нафталинсульфокислоты , отличающийс тем, что, с целью повышени выхода целевого продукта, взаимодействию с;5-диметиламино-1-нафталинсульфокислотой подвергают хлорсульфоновую кислоту, вз тую в мол рном соотношении с сульфокислотой A method for producing 5-dimethylamino-1-NAFTALINSULPHOLORIDE based on 5-dimethylamino-1-naphthalenesulfonic acid, characterized in that, in order to increase the yield of the target product, to interact with; sulphonic acid ratio
Description
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05 Изобретение относитс к усовершенствованному способу получени 5-диметиламино-1-нафталинсульфохлори да ( дансилхлорида/, который широко Используетс в органическом анализе дл идентификации аминов, аминокислот , пептидов и белков. Известен способ получени дансил хлорида, заключающийс в растирании в ступке 5-диметиламино-Ч-сульфокис лоты с п тихлористым фосфором. Выхо целевого продукта 25-40% Cl 3. Недостатком этого способа вл етс относительно невысокий выход целевого продукта. Наиболее близким к предлагаемому вл етс способ получени даисилфло да взаимодействием 5-диметиламино-1 -сульфокислоты с хлористым тионило в присутствии диметилформамида. Выход целевого продукта 60% 2. Недостатком этого способа вл ет с относительно невысокий выход целевого продукта. Цель изобретени - повьмение выхода целевого продукта, Поставленна цель достигаетс тем, что согласно способу получени дансилхлорида, заключающемус в том, что 5-диметиламино-1-нафталинСульфокислоту подвергают взаимодействию с хлорсульфоновой кислотой, вз тую в мол рном соотношении с сульфокислотой (7-10):1. Процесс ведут при комнатной температуре . Выход целевого продукта 82-84%. Пример. К20,4г (l5,5 ммоль/ хлорсульфоновой кислоты добавл ют при 20 С за 15 мин 4,4 г (1,5 ммоль/, 5-диметиламино-1-нафталинсульфокислоты , высушенной в течение 24 ч при 120°С, реакционный раствор перемешивают 15 мин, осторожно за 10-15 мин выливают в смесь 100 г измельченного льда, 40 г бикарбоната натри и 100 мл воды. Нейтрализованную реак- ционную смесь фильтруют, осадок промывают водой и дансилхлорид экстрагируют на фильтре этилацетатом. Экстракт сушат карбонатом.натри , упаривают, остаток сушат над п тиокисью фосфора и получают 4,1 г дансилхлорида . Выход 82,8%, т.пл. 66-67°c,i после JIepeкpиcтcшлизaции из смеси бензол-гексан т,пл, 68-69 С В Услови х примера при использовании 7-кратного избытка хлорсульфоновой кцслоты получают дансилхлорид с выходом 84%, а при использовании 5-кратного избытка выход составл ет 34%. Избыток хлорсульфоновой кислоты выше- 10-кратного практически не вли ет на выход целевого продукта по сравнению с использованием 7-10 крат:: ного избытка. Высокое качество полученного по предлагаемому методу дансилхлорида значйа-ельно упрощает его выделение, , причем получае№лй продукт практически не требует очистки.05 The invention relates to an improved method for the preparation of 5-dimethylamino-1-naphthalene sulfochloride (dansyl chloride), which is widely used in organic analysis to identify amines, amino acids, peptides and proteins. A known method for the preparation of dansyl chloride consists in grinding in a 5-dimethylamino mortar H-sulfoxides with phosphorus pentachloride. Output of the desired product is 25-40% Cl 3. The disadvantage of this method is the relatively low yield of the desired product. The closest to the one proposed is the method of obtaining and daylight by the interaction of 5-dimethylamino-1-sulfonic acid with thionyl chloride in the presence of dimethylformamide. The yield of the target product is 60%. 2. The disadvantage of this method is the relatively low yield of the target product. that according to the method for producing dansyl chloride, comprising the fact that 5-dimethylamino-1-naphthalene sulfonic acid is reacted with chlorosulfonic acid, taken in a molar ratio with sulfonic acid (7-10): 1. The process is carried out at room temperature. The yield of the target product 82-84%. Example. K20.4g (l5.5 mmol / chlorosulfonic acid was added at 20 ° C over 15 min. 4.4 g (1.5 mmol) of 5-dimethylamino-1-naphthalenesulfonic acid, dried for 24 hours at 120 ° C, the reaction solution mix for 15 minutes, carefully pour 10 g of crushed ice, 40 g of sodium bicarbonate and 100 ml of water into the mixture for 10-15 minutes. The neutralized reaction mixture is filtered, the precipitate is washed with water and dansyl chloride is extracted on the filter with ethyl acetate. The extract is dried with carbonate. evaporated, the residue is dried over phosphorus pentaoxide and 4.1 g of dansyl chloride are obtained, yield 82.8%, mp. 66-67 ° c, i after JI replication of the mixture from benzene-hexane mixture, mp 68-69 ° C. Under the conditions of the example, using a 7-fold excess chlorosulfonic acid, dansyl chloride is obtained with a yield of 84%, and using a 5-fold excess yield is 34%. An excess of 10-fold chlorosulfonic acid has almost no effect on the yield of the target product as compared to using a 7-10 fold excess. The high quality of the dansyl chloride method obtained by the method significantly simplifies its isolation, and get no product practically no traffic buet cleaning.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU823434737A SU1054346A1 (en) | 1982-03-01 | 1982-03-01 | Process for preparing 5-dimethylamino-1-naphthalene-sulfochloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU823434737A SU1054346A1 (en) | 1982-03-01 | 1982-03-01 | Process for preparing 5-dimethylamino-1-naphthalene-sulfochloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1054346A1 true SU1054346A1 (en) | 1983-11-15 |
Family
ID=21010656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU823434737A SU1054346A1 (en) | 1982-03-01 | 1982-03-01 | Process for preparing 5-dimethylamino-1-naphthalene-sulfochloride |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU1054346A1 (en) |
-
1982
- 1982-03-01 SU SU823434737A patent/SU1054346A1/en active
Non-Patent Citations (1)
| Title |
|---|
| 1. Weber G. polarization of F 1 uorescerlce of Macromolecules Biochera, J, 1952, V, 51, p. 155. 2. Rosshard H.H. et al. Eine Methode zur KataI уs1erter Herstellung von CarbonSaure-chloriden mit Vf hiony Ich lorid Helv. Chim. Acta, 1959, Bd. 42. S. 1953 (прототип). * |
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