Water → 4-[1-(1-Imidazolyl)butyl]-benzoic acid dimethylamide

HRID 727852Notes

Reaction equation

HRID 727852 reaction equation
[N:1]1([CH:6]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=2)[CH2:7][CH2:8][CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[CH2:19]([N:21]1CCOC[CH2:22]1)C.C(OC(Cl)=O)C(C)C.O>CN(C)C=O>[CH3:19][N:21]([CH3:22])[C:14](=[O:16])[C:13]1[CH:12]=[CH:11][C:10]([CH:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH2:7][CH2:8][CH3:9])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7525EthylmorpholineHCID 62365Isobutyl chloroformateHCID 145143684-[1-(1-Imidazolyl)-butyl]-benzoic acid

Product 1

HCID 145143834-[1-(1-Imidazolyl)butyl]-benzoic acid dimethylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1.2 g of 4-[1-(1-imidazolyl)-butyl]-benzoic acid is dissolved in 10 ml of dimethylformamide, mixed at 0° C. with 1 ml of N-ethylmorpholine and 1 ml of chloroformic acid isobutyl ester. It is stirred for 30 minutes at 0° C., 2 ml of dimethylamino solution is instilled and stirred for 2 hours at 0° C. It is stirred into 500 ml of water, extracted with ethyl acetate and the organic phase is concentrated by evaporation in a vacuum. The remaining residue is distilled on a bulb tube. Boiling point: 260° C./0.03 mbar. 0.9 g of 4-[1-(1-imidazolyl)butyl]-benzoic acid dimethylamide is obtained.

Workup

  1. stirringstirred for 2 hours at 0° C
  2. extractionextracted with ethyl acetate
  3. concentrationthe organic phase is concentrated by evaporation in a vacuum
  4. distillationThe remaining residue is distilled on a bulb tube

Sources & evidence

ORD record
ord-86aead17fd2244558fef82d6b9ad0e29
Source dataset
uspto-grants-1991_09
Patent number
US05045558

Reaction notes

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