p-Toluenesulfonic acid → HCID 21506067, 화합물

HRID 918667

반응식

HRID 918667 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:18](=[O:21])(=[O:20])[NH2:19])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6].[CH:22]1[C:27]([CH:28]=O)=[CH:26][C:25]2[O:30][CH2:31][O:32][C:24]=2[CH:23]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[H][H]>C(O)(=O)C.[Pt]=O>[CH2:31]1[O:32][C:24]2[CH:23]=[CH:22][C:27]([CH2:28][NH:1][C:2]3[CH:3]=[C:4]([CH:8]=[C:9]([S:18](=[O:21])(=[O:20])[NH2:19])[C:10]=3[O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]([OH:7])=[O:6])=[CH:26][C:25]=2[O:30]1

참가 물질

7

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 8438PiperonalHCID 1199273-Amino-4-phenoxy-5-sulfamoylbenzoic acidHCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 21506067HCID 21506067, 화합물

시약·촉매·용매 2

HCID 82844Platinum oxide (PtO)촉매HCID 176Acetic Acid용매

실험 절차

To a suspension of 3-amino-4-phenoxy-5-sulphamyl-benzoic acid (1.54 g) in acetic acid (30 ml), piperonal (0.75 g) was added. After the addition of platinum oxide (25 mg) and a catalytic amount of p-toluenesulphonic acid, the reaction mixture was hydrogenated at room temperature and 1.1 atmospheres hydrogen pressure until the hydrogen uptake had become negligible. Then the reaction mixture was filtered by suction. The filter cake was suspended in water (100 ml), and the pH was adjusted to 8.5 by addition of lithium hydroxide. After the catalyst had been removed from the resulting solution, the 3-(3,4-methylenedioxybenzylamino)-4-phenoxy-5-sulphamyl-benzoic acid was precipitated from the filtrate by addition of 4N hydrochloric acid until the pH was 3. After recrystallization from methanol, the melting point was 229°-230°C.

후처리

  1. additionwas added
  2. customwas hydrogenated at room temperature
  3. filtrationThen the reaction mixture was filtered by suction
  4. additionthe pH was adjusted to 8.5 by addition of lithium hydroxide
  5. customAfter the catalyst had been removed from the resulting solution
  6. customthe 3-(3,4-methylenedioxybenzylamino)-4-phenoxy-5-sulphamyl-benzoic acid was precipitated from the filtrate by addition of 4N hydrochloric acid until the pH was 3
  7. customAfter recrystallization from methanol

출처 및 근거

ORD 기록
ord-838e789611c743989ca0ae934ebf6d6b
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03971819

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