Formic Acid → HCID 178441481, compound

HRID 653727Notes

Reaction equation

HRID 653727 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[C:8]2[C:28]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:29][CH:30]=[CH:31][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].C(O)=[O:40]>C(O)CO.C(OCC)(=O)C>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:24][N:25]=[N:26][N:27]=3)=[CH:13][CH:12]=2)[C:8]2[C:28]([C:32]([O:34][CH2:35][CH2:36][OH:40])=[O:33])=[CH:29][CH:30]=[CH:31][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 24758Sodium hydrideHCID 178441479HCID 178441479, compound

Product 1

HCID 178441481HCID 178441481, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-butyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate (0.72 g) in ethylene glycol (15 ml) was added, while stirring at room temperature, sodium hydride (60% oil, 0.25 g) and the mixture was stirred at room temperature for 15 hours. To the reaction mixture was added ice-water (100 ml), which was made acidic with formic acid. Precipitates then formed were dissolved in ethyl acetate (100 ml) and the solution was washed with water, dried and concentrated to dryness to give a crystalline product. The crystals were recrystallized from acetone to afford colorless crystals (0.49 g, 66%), m.p. 145°-147° C.

Workup

  1. customPrecipitates
  2. customthen formed
  3. washthe solution was washed with water
  4. customdried
  5. concentrationconcentrated to dryness
  6. customto give a crystalline product
  7. customThe crystals were recrystallized from acetone

Sources & evidence

ORD record
ord-3b8fc99d5c034cf7816c75129aaeab87
Source dataset
uspto-grants-1992_07
Patent number
US05128356

Reaction notes

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