2,3-Diaminobenzoic acid → 2-(6-chloropyridin-3-yl)-1H-benzo[d]imidazole-4-carboxylic acid

HRID 85097

반응식

HRID 85097 반응식
[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][N:14]=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C.O>[Cl:12][C:13]1[N:14]=[CH:15][C:16]([C:17]2[NH:11][C:10]3[CH:9]=[CH:8][CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]=3[N:1]=2)=[CH:19][CH:20]=1

참가 물질

6

반응물 3

HCID 1980692,3-Diaminobenzoic acidHCID 656671Sodium PyrosulfiteHCID 27640536-Chloropyridine-3-carbaldehyde

생성물 1

HCID 866537842-(6-chloropyridin-3-yl)-1H-benzo[d]imidazole-4-carboxylic acid수율 95%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

2,3-Diaminobenzoic acid (1; 200 mg, 1.31 mmol), 6-chloronicotinaldehyde (5; 186 mg, 1.31 mmol), and Na2S2O5 (324 mg, 1.7 mmol) were taken up in DMF (10 mL) and stirred at 100° C. for 18 h. The reaction mixture was cooled to room temperature and diluted with H2O. The resulting mixture was stirred for 1 h at room temperature and filtered. The collected solids were washed with water, MeOH, and dried to afford 2-(6-chloropyridin-3-yl)-1H-benzo[d]imidazole-4-carboxylic acid 6 as a pale solid (340 mg, yield: 95%).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringThe resulting mixture was stirred for 1 h at room temperature
  3. filtrationfiltered
  4. washThe collected solids were washed with water, MeOH
  5. customdried

출처 및 근거

ORD 기록
ord-3bbdb06af4854b2e8c9351df230baf00
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846947B2

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