Formic Acid → HCID 19094223, compound

HRID 487187Notes

Reaction equation

HRID 487187 reaction equation
[Br:1][C:2]1[CH:22]=[C:21]([C:23]([OH:25])=[O:24])[C:5]2[N:6]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:7]([CH2:9][CH2:10][CH2:11][CH3:12])=[N:8][C:4]=2[CH:3]=1.Cl.[CH:27](Cl)(Cl)Cl.CO.C(O)=O>CO>[Br:1][C:2]1[CH:22]=[C:21]([C:23]([O:25][CH3:27])=[O:24])[C:5]2[N:6]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:7]([CH2:9][CH2:10][CH2:11][CH3:12])=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 9888459HCID 9888459, compoundHCID 21584188Chloroform methanol

Product 1

HCID 19094223HCID 19094223, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-bromo-2-n-butyl-1-(2-chlorophenyl)-methyl-1H-benzimidazole-7-carboxylic acid (prepared in Example 1)(1.0 g, 2.4 mmol) in methanol (15 mL) was cooled in ice and then saturated with dry hydrochloric acid. The reaction mixture was refluxed for 14 hours, and TLC on silica with 9:1 chloroform/methanol containing a trace of formic acid gave an Rf 0.87 for the product; the starting material had an Rf 0.65. The methanol was evaporated, the residue was diluted with ice water and the solid was separated, washed with water and dried at 92° C. at high vacuum to provide 0.88 g of methyl 5-bromo-2-n-butyl-1-(2-chlorophenyl)methyl-1H-benzimidazole-7-carboxylate.

Workup

  1. temperaturewas cooled in ice
  2. temperatureThe reaction mixture was refluxed for 14 hours
  3. customThe methanol was evaporated
  4. additionthe residue was diluted with ice water
  5. customthe solid was separated
  6. washwashed with water
  7. customdried at 92° C. at high vacuum

Sources & evidence

ORD record
ord-05126a8cf530495fb0be17fb600df862
Source dataset
uspto-grants-1994_03
Patent number
US05294631

Reaction notes

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