JPH0524897B2 - - Google Patents
Info
- Publication number
- JPH0524897B2 JPH0524897B2 JP26893084A JP26893084A JPH0524897B2 JP H0524897 B2 JPH0524897 B2 JP H0524897B2 JP 26893084 A JP26893084 A JP 26893084A JP 26893084 A JP26893084 A JP 26893084A JP H0524897 B2 JPH0524897 B2 JP H0524897B2
- Authority
- JP
- Japan
- Prior art keywords
- aminobenzoic acid
- added
- reaction
- water
- acid
- 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
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 23
- 229960004050 aminobenzoic acid Drugs 0.000 claims description 13
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 claims description 9
- OBROJPONABYYMT-UHFFFAOYSA-N 4-(4,5-dihydro-1h-imidazol-2-ylamino)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NCCN1 OBROJPONABYYMT-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- SHZDNDYYTPHCKI-UHFFFAOYSA-N 4-(4,5-dihydro-1H-imidazol-2-ylamino)benzoic acid methanesulfonic acid Chemical compound CS(O)(=O)=O.C1=CC(C(=O)O)=CC=C1NC1=NCCN1 SHZDNDYYTPHCKI-UHFFFAOYSA-N 0.000 description 1
- WDADGTXRTQBRLY-UHFFFAOYSA-N 4-(4,5-dihydro-1h-imidazol-2-ylamino)benzoic acid;hydrochloride Chemical compound Cl.C1=CC(C(=O)O)=CC=C1NC1=NCCN1 WDADGTXRTQBRLY-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- -1 N-2-imidazolinylidene-p-aminobenzoic acid Chemical compound 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- XETSAYZRDCRPJY-UHFFFAOYSA-M sodium;4-aminobenzoate Chemical compound [Na+].NC1=CC=C(C([O-])=O)C=C1 XETSAYZRDCRPJY-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26893084A JPS61148165A (ja) | 1984-12-20 | 1984-12-20 | Ｎ―２―イミダゾリジニリデン―ｐ―アミノ安息香酸の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26893084A JPS61148165A (ja) | 1984-12-20 | 1984-12-20 | Ｎ―２―イミダゾリジニリデン―ｐ―アミノ安息香酸の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61148165A JPS61148165A (ja) | 1986-07-05 |
| JPH0524897B2 true JPH0524897B2 (enrdf_load_stackoverflow) | 1993-04-09 |
Family
ID=17465250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26893084A Granted JPS61148165A (ja) | 1984-12-20 | 1984-12-20 | Ｎ―２―イミダゾリジニリデン―ｐ―アミノ安息香酸の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61148165A (enrdf_load_stackoverflow) |
-
1984
- 1984-12-20 JP JP26893084A patent/JPS61148165A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61148165A (ja) | 1986-07-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2287521C2 (ru) | Очистка 2-нитро-4-метилсульфонилбензойной кислоты | |
| US2665313A (en) | Production of 1, 6-naphthalenediol | |
| JPH0524897B2 (enrdf_load_stackoverflow) | ||
| JP3003287B2 (ja) | Ｎ−アルキルアミノエタンスルホン酸ナトリウムの製法 | |
| SU1129204A1 (ru) | Способ получени сернокислотной пасты 1,5-диокси-2,6-дисульфоантрахинона | |
| JPH08291135A (ja) | タウリン類縁体の製造方法 | |
| JP2915515B2 (ja) | Ｏ―メチルイソ尿素硫酸塩の製造方法 | |
| JPH0597782A (ja) | 塩酸ベバントロールの製造方法 | |
| US4247693A (en) | Process for preparing 2,4,5,6-tetraaminopyrimidine sulfate | |
| KR0129550B1 (ko) | 아미노카르보닐 치환 피리딘술핀산 또는 그의 염 | |
| JP2931393B2 (ja) | ２−アミノベンゼン−１，４−ジスルホン酸の製法 | |
| US4461918A (en) | Process for producing pentachloronitrobenzene from hexachlorobenzene | |
| KR810000879B1 (ko) | 디아세톤-2-케토- l-굴론산의 제조방법 | |
| JPS62288102A (ja) | ジシアナミド金属塩の製造方法 | |
| US4454362A (en) | Process for producing pentachloronitrobenzene | |
| KR20040015025A (ko) | 페닐렌-비스-벤즈이미다졸-테트라설폰산 이나트륨 염의제조 방법 | |
| JPH045252A (ja) | ４，４’‐ジヒドロキシ‐３，３’，５，５’‐テトラメチルジフェニルメタンの製造方法 | |
| JPH10316646A (ja) | 高純度の結晶質ｏ−メチルイソ尿素酢酸塩の製造方法及び該方法で得られた結晶質ｏ−メチルイソ尿素酢酸塩 | |
| JPS5910656B2 (ja) | １−アミノ−ナフタレン−７−スルホン酸の製造方法 | |
| JP3093109B2 (ja) | １−アザ−６−クロロ−８−メチル−４−チオ−（３ｈ）−ナフタレン−２−オンの製造方法 | |
| JP3148484B2 (ja) | １−アミノ−５−ベンゾイルアミノアントラキノンの製造法 | |
| JPH0455184B2 (enrdf_load_stackoverflow) | ||
| JPS62164660A (ja) | ２−スルフアミド安息香酸メチルエステルの製造方法 | |
| JPS63225352A (ja) | ２，７−ナフタレンジスルホン酸の製造方法 | |
| JPH10168045A (ja) | エチレンジアミン−ｎ，ｎ’−ジコハク酸およびその第二鉄錯塩の製法 |