Ammonia → 5-Methyl-2-phenyl-4-imidazoleacetamide hydrate

HRID 1580095Notes

Reaction equation

HRID 1580095 reaction equation
[CH3:1][C:2]1[NH:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][C:14]#[N:15].S(=O)(=O)(O)[OH:17].N>>[OH2:17].[CH3:1][C:2]1[NH:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][C:14]([NH2:15])=[O:17]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 65475Mefenidil

Product 1

HCID 215650795-Methyl-2-phenyl-4-imidazoleacetamide hydrate

Procedure

A mixture of 9.86 (0.05 mole of 5-methyl-2-phenyl-4-imidazoleacetonitrile and 15 ml of concentrated sulfuric acid is stirred and warmed on a steam bath until solution is complete (about 25 minutes). The warm mixture is poured onto excess ice and basified with a slight excess of concentrated aqueous ammonia. Recrystallization from ethanol (95%)-water affords the product, 5-methyl-2-phenyl-4-imidazoleacetamide hydrate, m.p. 186°-188°C. The melting point can be changed to 202°-4°C by thoroughly grinding in an agate mortar. The product can also be made to melt over the range of about 186°-204°C by very slowly raising the oilbath temperature. Treatment with mineral acid, e.g., sulfuric or hydrobromic acid, affords the corresponding acid addition salt.

Workup

  1. temperaturewarmed on a steam bath until solution
  2. custom(about 25 minutes)
  3. additionThe warm mixture is poured onto excess ice
  4. customRecrystallization from ethanol (95%)-water

Sources & evidence

ORD record
ord-960b3f6ec0b244e0b3fa41ef78545eb1
Source dataset
uspto-grants-1976_01
Patent number
US03932445

Reaction notes

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