Water → 2-[4-(2-Methoxycarbonyl-2-methyl-propyl)-2,6-dimethyl-phenyl]-3H-benzoimidazole-5-carboxylic acid

HRID 1360799Notes

Reaction equation

HRID 1360799 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([OH:11])=[O:10])[CH:5]=[CH:6][C:7]=1[NH2:8].[CH3:12][O:13][C:14](=[O:29])[C:15]([CH3:28])([CH3:27])[CH2:16][C:17]1[CH:22]=[C:21]([CH3:23])[C:20]([CH:24]=O)=[C:19]([CH3:26])[CH:18]=1.OOS([O-])=O.[K+].O>CN(C=O)C>[CH3:12][O:13][C:14]([C:15]([CH3:28])([CH3:27])[CH2:16][C:17]1[CH:18]=[C:19]([CH3:26])[C:20]([C:24]2[NH:1][C:2]3[CH:3]=[C:4]([C:9]([OH:11])=[O:10])[CH:5]=[CH:6][C:7]=3[N:8]=2)=[C:21]([CH3:23])[CH:22]=1)=[O:29]

Participants

6

Reactant 4

HCID 962Water2×HCID 692633,4-Diaminobenzoic acidHCID 23707502Potassium hydroxy sulfiteHCID 86632822Methyl 3-(4-formyl-3,5-dimethylphenyl)-2,2-dimethylpropanoate

Product 1

HCID 669667662-[4-(2-Methoxycarbonyl-2-methyl-propyl)-2,6-dimethyl-phenyl]-3H-benzoimidazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

7.6 g of 3,4-diaminobenzenoic acid was stirred in 120 ml of DMF at room temperature. It was treated with 12.4 g of 3-(4-formyl-3,5-dimethyl-phenyl)-2,2-dimethyl-propionic acid methyl ester (the intermediate A in Example 1-62) followed by an addition of a slurry of 15 g of Oxone in 60 ml of DMF. The reaction was stirred at room temperature for 3 h and 60 mL of water was added and the pH was adjusted to 6. Additional 150 mL of water was added and the resulting precipitates were collected by filtration. The collected precipitates were washed with water and dried under vacuum to afford the title compound.

Workup

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration
  3. customThe collected precipitates
  4. washwere washed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-e5028e1fb88d4206ac3dc7b2f6be5c34
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

Loading…