Ethanol → HCID 178497341, compound

HRID 1586089Notes

Reaction equation

HRID 1586089 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS([O-])=O.[Na+].[CH3:21][O:22][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[C:26]([NH2:31])[CH:25]=1.C(O)C>O>[O:1]([C:8]1[CH:15]=[CH:14][C:11]([C:12]2[NH:30][C:27]3[CH:28]=[CH:29][C:24]([C:23]([O:22][CH3:21])=[O:32])=[CH:25][C:26]=3[N:31]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 661394-PhenoxybenzaldehydeHCID 1355243,5-Diamino-2-methylbenzoic acidHCID 23665763Sodium Bisulfite

Product 1

HCID 178497341HCID 178497341, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To 4-phenoxybenzaldehyde (3.0 g, 0.02 mol) was added 21 mL of 40% NaHSO3 (aq). The mixture was stirred for 1 h at 25° C. Methyl-3,4-diaminobenzoate (2.5 g, 0.02 mol) and ethanol (15 mL) were added. The mixture was refluxed for 4 h. The reaction was then poured into water. The precipitate filtered and recrystallized from EtOAc to afford 2-(4-phenoxyphenyl)-1H-benzimidazole-5-carboxylic acid, methyl ester (5.06 g, 97%) as a white solid.

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. filtrationThe precipitate filtered
  3. customrecrystallized from EtOAc

Sources & evidence

ORD record
ord-1304c3a2b3654b5dad863e16e79e31dc
Source dataset
uspto-grants-1999_08
Patent number
US05942532

Reaction notes

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