SU332621A1 - - Google Patents
Info
- Publication number
- SU332621A1 SU332621A1 SU1277227A SU1277227A SU332621A1 SU 332621 A1 SU332621 A1 SU 332621A1 SU 1277227 A SU1277227 A SU 1277227A SU 1277227 A SU1277227 A SU 1277227A SU 332621 A1 SU332621 A1 SU 332621A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mol
- alkyl
- benzene
- urea derivatives
- urea
- Prior art date
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 150000003672 ureas Chemical class 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- -1 alkenyl halide Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SKAADKSETAYKGL-UHFFFAOYSA-N 1-methyl-1-phenylurea Chemical compound NC(=O)N(C)C1=CC=CC=C1 SKAADKSETAYKGL-UHFFFAOYSA-N 0.000 description 1
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N Fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
- 125000004849 alkoxymethyl group Chemical group 0.000 description 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N carbamoyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Description
СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ МОЧЕВИНЫMETHOD OF OBTAINING UREA DERIVATIVES
Изобретение относитс к способу получени неизвестных ранее производных мочевины общей формулыThis invention relates to a process for the preparation of previously unknown urea derivatives of the general formula
г g
(i-oJnX Ra 4)а,(i-oJnX Ra 4) a,
где RI - галоидный алкил или циклоалкил, галоидный алкенил или циклоалкеннл, причем П1 1 или 2;where RI is alkyl halide or cycloalkyl, alkenyl halide or cycloalkenne, moreover, A1 or 2;
Ra и Нз - водород, алкил или алкоксигрулпа с 1-4 атомами углерода, причем На и Ra не вл ютс одновремеппо водородом;Ra and Hz are hydrogen, alkyl or alkoxygrup with 1-4 carbon atoms, and Ha and Ra are not simultaneously hydrogen;
R4 -галоид, алкил, алкокси- или трифторметильна группа, причем , которые могут найти применение в качестве физиологически активных веществ.R4-halide, alkyl, alkoxy or trifluoromethyl group, moreover, which can be used as physiologically active substances.
Способ получени вышеуказанных производных мочевины состоит в том, что соответ . ственно замещенный феноламин подвергают взаимодействию с соответствующим алкилизоцианатом или хлорангидридом карбаминовой кислоты в среде органического растворител , например бензоле, толуоле, диоксане или диметилформамиде .The method for producing the above urea derivatives is that. The physically substituted phenolamine is reacted with an appropriate alkyl isocyanate or carbamic acid chloride in an organic solvent medium, for example, benzene, toluene, dioxane or dimethylformamide.
Производные мочевины, полученные но предложенному способу, вл ютс почти исключительно кристаллическими продуктами, очистка которых производитс путем нерекристаллизации из органических растворителей .The urea derivatives produced by the proposed method are almost exclusively crystalline products, which are purified by non-recrystallization from organic solvents.
Пример 1. М-4-(3,3-Дихлораллнлокси)фенил -N-метилмочевина .Example 1. M-4- (3,3-Dichlorallnloxy) phenyl-N-methyl urea.
44 г (0,2 моль) 4-(3,3-дихлораллилокси)анилина раствор ют при комнатной температуре в 100 мл абсолютного бензола и затем при номещивании добавл ют 11 г (0,22 моль) метилизоцианата. После реакции в течение 1 час, проводимой при температуре 40°С, выпавщий продукт реакции отжимают на путче, промывают в небольщом количестве бензола и высущивают. Выход продукта 38 г, т. пл. 142-144°С.44 g (0.2 mol) of 4- (3,3-dichloroaryloxy) aniline is dissolved at room temperature in 100 ml of absolute benzene and then 11 g (0.22 mol) of methyl isocyanate are added during nesting. After reaction for 1 hour, carried out at a temperature of 40 ° C, the precipitated product of the reaction is squeezed onto a putsch, washed with a small amount of benzene and dried. The product yield 38 g, so pl. 142-144 ° C.
Вычислено, %: CI 25,8; N 10,2.Calculated,%: CI 25.8; N 10.2.
CuHi2Cl2N202CuHi2Cl2N202
Найдено, %: С1 25,6; N 10,3.Found,%: C1 25.6; N 10.3.
Мол. вес 275.Mol weight 275.
Пример 2. (Г,2-Дихлорвипилокси)фенил -Ы ,Ы-диметил мочевина. 30 г (0,15 моль 4-(Г,-дихлорвинилокси)аиилииа раствор ют ири комнатной температуре в 50 мл абсолютного бензола и добавл ют 16 г (0,16 моль) триэтиламина. ЗатемExample 2. (G, 2-Dichlorovipyloxy) phenyl-N, N-dimethyl urea. 30 g (0.15 mol of 4- (G, -dichlorvinyloxy) ailium) are dissolved at room temperature in 50 ml of absolute benzene and 16 g (0.16 mol) of triethylamine are added. Then
Publications (1)
| Publication Number | Publication Date |
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| SU332621A1 true SU332621A1 (en) |
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