Dimethylformamide → HCID 13654296, compound

HRID 844917Notes

Reaction equation

HRID 844917 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[N:11]1[C:15]([C:16]([OH:18])=O)=[CH:14][N:13]=[CH:12]1)[CH3:2].S(Cl)(Cl)=O.C[N:24](C)C=O>>[CH2:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[N:11]1[C:15]([C:16]([NH2:24])=[O:18])=[CH:14][N:13]=[CH:12]1)[CH3:10]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 13252199HCID 13252199, compound

Product 1

HCID 13654296HCID 13654296, compoundYield 83%

Conditions

Temperature
80 °C

Procedure

24.4 g (0.1 mol) of 1-(2,6-diethylphenyl)-imidazole-5carboxylic acid were added in portions to 36 g (0.3 mol) of thionyl chloride and 1 ml of dimethylformamide. After the addition, the mixture was heated at 80° C. until the evolution of gas had ended, and the solid residue was dried in vacuo and introduced in portions into 150 ml of ice-cold concentrated aqueous ammonia solution with thorough stirring. The mixture was stirred at room temperature for 1 hour; the precipitate was filtered off and dried. 20.2 g of 1-(2,6-diethylphenyl)-imidazole-5-carboxamide were obtained as a colorless solid of melting point 171°-171.5° C. (ethyl acetate/hexane); yield: 83% of theory.

Workup

  1. additionAfter the addition
  2. customthe solid residue was dried in vacuo
  3. additionintroduced in portions into 150 ml of ice-cold concentrated aqueous ammonia solution with thorough stirring
  4. filtrationthe precipitate was filtered off
  5. customdried

Sources & evidence

ORD record
ord-2f86b0e062c84a62a90801b24d1f9d72
Source dataset
uspto-grants-1988_07
Patent number
US04755213

Reaction notes

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