Hydrochloric Acid → 2-(2,4-dichloro-phenyl)-7-hydroxy-1H-benzoimidazole-4-carboxylic acid

HRID 349478Notes

Reaction equation

HRID 349478 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[NH:10][C:9]=2[C:8]([O:22]C)=[CH:7][CH:6]=1)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1(C)C=CC=CC=1>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[C:11]1[NH:10][C:9]2[C:8]([OH:22])=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:13]=2[N:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 691199112-(2,4-dichloro-phenyl)-7-methoxy-1H-benzoimidazole-4-carboxylic acid methyl ester

Product 1

HCID 691199912-(2,4-dichloro-phenyl)-7-hydroxy-1H-benzoimidazole-4-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(2,4-dichloro-phenyl)-7-methoxy-1H-benzoimidazole-4-carboxylic acid methyl ester (1.9 g, 5.47 mmol) obtained in step 2 was dissolved in 100 ml of toluene, aluminum chloride (3.61 g, 27.05 mmol) was added thereto and refluxed for 8 hours. The resulting solution was cooled to room temperature, the reaction was stopped by adding 3 N HCl thereto and stirred for 30 min. The precipitate formed was filtered, washed with benzene and dried to obtain the title compound (1.63 g, 5.03 mmol) in a yield of 92%.

Workup

  1. temperaturerefluxed for 8 hours
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. washwashed with benzene
  5. customdried

Sources & evidence

ORD record
ord-f269b1d085f34749a528b155c8330c5b
Source dataset
uspto-grants-2007_02
Patent number
US07179832B2

Reaction notes

Loading…