3,4-Diaminobenzoic acid → 2-(4-methoxycarbonylmethoxy-2,6-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid

HRID 1515036노트

반응식

HRID 1515036 반응식
[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH:13]=O)=[C:8]([CH3:15])[CH:7]=1.[NH2:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[NH2:27])[C:21]([OH:23])=[O:22]>CS(C)=O>[CH3:1][O:2][C:3]([CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:17][C:18]3[CH:19]=[C:20]([C:21]([OH:23])=[O:22])[CH:24]=[CH:25][C:26]=3[N:27]=2)=[C:8]([CH3:15])[CH:7]=1)=[O:16]

참가 물질

4

반응물 2

HCID 692633,4-Diaminobenzoic acidHCID 86651272(4-Formyl-3,5-dimethylphenoxy)-acetic acid methyl ester

생성물 1

HCID 669656912-(4-methoxycarbonylmethoxy-2,6-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution (4-formyl-3,5-dimethylphenoxy)-acetic acid methyl ester (2.4 g) (from Example 6-9) and 3,4-diaminobenzoic acid (2.0 g) in DMSO (30 mL) under air at ambient temperature was added FeCl3 (150 mg) and the resulting brown reaction mixture was stirred at the same temperature overnight. The reaction was monitored by LC/MS which indicated completion. The reaction mixture was then decanted into 400 mL of stirred water and the resulting precipitate was collected by filtration and washed with water. The crude product was dried in the suction funnel for 4 h to give 2-(4-methoxycarbonylmethoxy-2,6-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid. MS (ESI) m/z 355.04 (M+H); Retention time=0.79 min (Method 10).

후처리

  1. customThe reaction mixture was then decanted into 400 mL of stirred water
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with water
  4. dry with materialThe crude product was dried in the suction funnel for 4 h

출처 및 근거

ORD 기록
ord-acde3ddf0be04c87a5937fa117d89b97
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222248B2

반응 노트

불러오는 중…