Water → 1H-Benzimidazole-1-butanoic acid, 2,3-dihydro-2-oxo-, ethyl ester

HRID 1381097Notes

Reaction equation

HRID 1381097 reaction equation
CC([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:5]1=[O:21])=C.S(=O)(=O)(O)O.[OH-].[Na+].O>C(O)C>[O:21]=[C:5]1[N:6]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 23323468Ethyl 4-[2-oxo-3-(prop-1-en-2-yl)-2,3-dihydro-1H-benzimidazol-1-yl]butanoate

Product 1

HCID 103997611H-Benzimidazole-1-butanoic acid, 2,3-dihydro-2-oxo-, ethyl esterYield 81.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

31.4 g of the product of Step A were added at 0° to 5° C. to a mixture of 15.5 ml of sulfuric acid in 155 ml of ethanol and the mixture was stirred at 0° to 5° C. for 5 hours. The mixture was neutralized with sodium hydroxide and was poured into 1.5 liters of iced water. The mixture was stirred for 5 minutes and was vacuum filtered. The product was washed with water to obtain 22 g of ethyl 2,3-dihydro-2-oxo-1H-benzimidazol-1-butanoate melting at 88° C.

Workup

  1. stirringThe mixture was stirred for 5 minutes
  2. filtrationfiltered
  3. washThe product was washed with water

Sources & evidence

ORD record
ord-7ac14c003d544b40ae09d51b702b0acf
Source dataset
uspto-grants-1986_04
Patent number
US04585770

Reaction notes

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