HCID 19094213, compound → HCID 19094242, compound

HRID 487186Notes

Reaction equation

HRID 487186 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=1[NH:19][C:20](=O)[CH2:21][CH2:22][CH2:23][CH3:24].NC1C=C(C=CC=1NCC1C=CC=CC=1Cl)C(O)=O.C([NH-])(=O)CCCC>C(O)(=O)C>[CH2:21]([C:20]1[N:9]([CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=2[N:19]=1)[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 19094213HCID 19094213, compoundHCID 19094220HCID 19094220, compoundHCID 178446832HCID 178446832, compound

Product 1

HCID 19094242HCID 19094242, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The procedure of example 2(iii) was followed to prepare the amide, 4-[(2-chlorophenyl)methyl]amino-3-(valeryl)aminobenzoic acid, from 3-amino-4-[(2-chlorophenyl)methyl]aminobenzoic acid. The valeryl amide melted at 207°-209° C. (from ethyl acetate/hexane). This amide (0.39 g, 1.08 mmol) was refluxed in acetic acid (2.5 mL) for 3 hours, the acetic acid was evaporated, water was added and the resulting solid was filtered and washed with water. Crystallization from methanol provided 0.3 g (81%) of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-benzimidazole-5-carboxylic acid; mp 238°-239° C.

Workup

  1. customthe acetic acid was evaporated
  2. additionwater was added
  3. filtrationthe resulting solid was filtered
  4. washwashed with water
  5. customCrystallization from methanol

Sources & evidence

ORD record
ord-b2790ff3925d46ff9b0e28060b585e85
Source dataset
uspto-grants-1994_03
Patent number
US05294631

Reaction notes

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