Dichloromethane → 3-chloro-N-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2-nitrophenyl]benzeneacetamide

HRID 1086205Notes

Reaction equation

HRID 1086205 reaction equation
[N:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)[CH:7]([CH3:9])[CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1.ClCCl.[Cl:23][C:24]1[CH:25]=[C:26]([CH2:30][C:31](Cl)=[O:32])[CH:27]=[CH:28][CH:29]=1>C(N(CC)CC)C>[Cl:23][C:24]1[CH:25]=[C:26]([CH2:30][C:31]([NH:16][C:13]2[CH:14]=[CH:15][C:10]([CH:6]([N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)[CH:7]([CH3:9])[CH3:8])=[CH:11][C:12]=2[N+:17]([O-:19])=[O:18])=[O:32])[CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 106552492-(3-chlorophenyl)acetyl ChlorideHCID 145184254-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2-nitrobenzenamine

Product 1

HCID 198758793-chloro-N-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2-nitrophenyl]benzeneacetamideYield 100%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 13 parts of 4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2-nitrobenzenamine in 195 parts of dichloromethane was added a solution of 19 parts of 3-chlorobenzeneacetyl chloride in 65 parts of dichloromethane. After stirring for 4 hours at room temperature, 10.1 parts of N,N-diethylethanamine were added. The reaction mixture was washed with water, dried, filtered and evaporated, yielding 39 parts (100%) of 3-chloro-N-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2-nitrophenyl]benzeneacetamide as an oily residue (interm. 100).

Workup

  1. washThe reaction mixture was washed with water
  2. customdried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-6df67ee7956f4b6b8bb422084bab6d19
Source dataset
uspto-grants-1991_07
Patent number
US05028606

Reaction notes

Loading…