Potassium Carbonate → HCID 131718409, compound

HRID 1033894Notes

Reaction equation

HRID 1033894 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[C:7](/[CH:10]=[C:11](\[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)/[C:12]([OH:14])=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].Cl[CH2:31][C:32]([N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])=[O:33].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[C:7](/[CH:10]=[C:11](\[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)/[C:12]([O:14][CH2:31][C:32]([N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])=[O:33])=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 16844Chloro-N,N-diethylacetamideHCID 9978845HCID 9978845, compound

Product 1

HCID 131718409HCID 131718409, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(benzyl)-2-propenoic acid (Example 2) (2.05 g, 5 mmol) in dry dimethylformamide (10 mL) was treated with 2-chloro-N,N-diethylacetamide (0.825 g, 5.51 mmol) followed by powdered potassium carbonate. This mixture was heated at 70° C. for 7 hours, diluted with water and extracted with ethyl acetate. The water-washed, dried, concentrated product solidified and after trituration with ether/hexane afforded 2.04 g (78%) of the title ester; mp 76°-77° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe water-washed
  3. customdried

Sources & evidence

ORD record
ord-d9a8652f7ed041e8a9574ecdb62b5c85
Source dataset
uspto-grants-1994_05
Patent number
US05312828

Reaction notes

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