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

HRID 1515036Notes

Reaction equation

HRID 1515036 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-acde3ddf0be04c87a5937fa117d89b97
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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