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

HRID 1515036ノート

反応式

HRID 1515036 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-acde3ddf0be04c87a5937fa117d89b97
出典データセット
uspto-grants-2012_07
特許番号
US08222248B2

反応ノート

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