JPH0469156B2 - - Google Patents
Info
- Publication number
- JPH0469156B2 JPH0469156B2 JP59039458A JP3945884A JPH0469156B2 JP H0469156 B2 JPH0469156 B2 JP H0469156B2 JP 59039458 A JP59039458 A JP 59039458A JP 3945884 A JP3945884 A JP 3945884A JP H0469156 B2 JPH0469156 B2 JP H0469156B2
- Authority
- JP
- Japan
- Prior art keywords
- mol
- salt
- absorption
- diamino
- yield
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 8
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims description 6
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 5
- 229940073608 benzyl chloride Drugs 0.000 claims description 5
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 150000003839 salts Chemical class 0.000 description 14
- 238000010521 absorption reaction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- -1 imidazolium compound Chemical class 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- ZXLYUNPVVODNRE-UHFFFAOYSA-N 6-ethenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=C)=N1 ZXLYUNPVVODNRE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59039458A JPS60184076A (ja) | 1984-02-29 | 1984-02-29 | 新規イミダゾリウム化合物及び該化合物の合成方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59039458A JPS60184076A (ja) | 1984-02-29 | 1984-02-29 | 新規イミダゾリウム化合物及び該化合物の合成方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60184076A JPS60184076A (ja) | 1985-09-19 |
| JPH0469156B2 true JPH0469156B2 (xx) | 1992-11-05 |
Family
ID=12553596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59039458A Granted JPS60184076A (ja) | 1984-02-29 | 1984-02-29 | 新規イミダゾリウム化合物及び該化合物の合成方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60184076A (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1554253A4 (en) * | 2002-06-03 | 2006-09-20 | Smithkline Beecham Corp | IMIDAZOLIUM COMPOUNDS INHIBITORS OF CXCR3 |
| JP2008133248A (ja) * | 2006-10-24 | 2008-06-12 | Sanyo Chem Ind Ltd | イミダゾリウム塩の製造方法 |
-
1984
- 1984-02-29 JP JP59039458A patent/JPS60184076A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60184076A (ja) | 1985-09-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4122277A (en) | 2-Tolyl-4,5-dihydroxymethyl imidazole | |
| JPH0469156B2 (xx) | ||
| HU185457B (en) | Process for preparating cimetidine-z | |
| WO2009017288A1 (en) | Process for preparation of disodium stilbenedisulfonates | |
| KR102702677B1 (ko) | 피마살탄 및 그의 제조 중간체의 제조방법 | |
| JP2851162B2 (ja) | 低塩化物イオン１，２，４―トリアゾール―５―オンの改良製造方法 | |
| JPS62155268A (ja) | ナイザチジンの合成法 | |
| JPS6360969A (ja) | イミダゾ−ル誘導体の製造方法 | |
| JP2811525B2 (ja) | ２−ブチル−４−クロロ−５−フォルミルイミダゾールの合成方法 | |
| JP3477631B2 (ja) | １，３−ビス（３−アミノプロピル）−１，１，３，３−テトラオルガノジシロキサンの精製方法 | |
| US3427315A (en) | Process for preparing purine derivatives | |
| JPS6156224B2 (xx) | ||
| JPH072742A (ja) | ４−アミノ−３−メチル−Ｎ−エチル−Ｎ−（β−ヒドロキシエチル）アニリン硫酸塩の新規製造法 | |
| EP0621260B1 (en) | Process for producing N,N-disubstituted p-phenylenediamine derivative sulphate | |
| JPS6317869A (ja) | ２−低級アルキル−４−アミノ−５−ホルミルピリミジンの製造法 | |
| JP4739695B2 (ja) | ５−アミノ―１―置換―１，２，４―トリアゾールの製造方法、及び該製造方法で得られるトリアゾール誘導体 | |
| JPS6210500B2 (xx) | ||
| KR800000717B1 (ko) | N”-시아노-n-메틸-n′-[2-(5-메틸이미다졸-4-일)-메틸티오]에틸구아니딘의 제조방법 | |
| RU2032681C1 (ru) | Способ получения 1-(2-[(5-диметиламинометил-2-фурил) -метилтио]-этил)-амино-1- метиламино-2-нитроэтилена | |
| JP3184745B2 (ja) | ビスウレア化合物およびその製造方法 | |
| JP3155909B2 (ja) | １，３−ジアルキル−２−イミダゾリジノン類の製造方法 | |
| CA1120493A (en) | Process for producing 4'-(2-carboxy-ethyl)phenyl trans-4-aminomethylcyclohexanecarboxylate or the acid-addition salts thereof and intermediates for producing the same | |
| HU185298B (en) | Process for producing cimetidine | |
| JPH0379345B2 (xx) | ||
| JPS59163396A (ja) | ５−（２−ハロゲノビニル）ウラシルヌクレオシドの製造法 |