Acetoxyacetyl chloride → HCID 178476484, compound

HRID 1595402Notes

Reaction equation

HRID 1595402 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[C:11]([C:13]([NH:15][C:16]3[S:17][CH:18]=[CH:19][N:20]=3)=[O:14])[N:12]=2)=[CH:4][CH:3]=1.[C:28]([O:31][CH2:32][C:33](Cl)=[O:34])(=[O:30])[CH3:29]>N1C=CC=CC=1>[C:28]([O:31][CH2:32][C:33](=[O:34])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:21]3[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=3)=[C:11]([C:13](=[O:14])[NH:15][C:16]3[S:17][CH:18]=[CH:19][N:20]=3)[N:12]=2)=[CH:4][CH:3]=1)(=[O:30])[CH3:29]

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 178424019HCID 178424019, compound

Product 1

HCID 178476484HCID 178476484, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(4-Aminophenyl)-5-(4-methylphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (0.30 g) obtained in Example 21 was dissolved in pyridine (20 ml) and acetoxyacetyl chloride (0.1 ml) was added dropwise under ice-cooling. The mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated and the residue was purified by silica gel chromatography using, as a mobile phase, chloroform/ethyl acetate=20:1. Theresidue was recrystallized from ethyl acetate to give 4-[5-(4-methylphenyl)-4-(2-thiazolylcarbamoyl)imidazol-2-yl]phenylcarbamoylmethyl acetate (0.13 g), melting point 250° C. or above.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by silica gel chromatography
  4. customTheresidue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ef9cd3cd73da433da1a6c47031c44b11
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

Loading…