o-Tolyl-acetyl chloride → HCID 19875848, compound

HRID 1886350Notes

Reaction equation

HRID 1886350 reaction equation
[N:1]1([CH:6]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)[CH2:7][CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][C:27](Cl)=[O:28]>ClCCCl>[N:1]1([CH:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:27](=[O:28])[CH2:26][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH3:19])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)[CH2:7][CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 2760632o-Tolyl-acetyl chlorideHCID 19875855HCID 19875855, compound

Product 1

HCID 19875848HCID 19875848, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred and cooled (0° C.) solution of 7 parts of 4-[1-(1H-imidazol-1-yl)propyl]-2-nitrobenzenamine in 126 parts of 1,2-dichloroethane were added 9.6 parts of 2-methylbenzeneacetyl chloride. After stirring for 12 hours at room temperature, the reaction mixture was poured into ice water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated in vacuo. The oily residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (98:2 by volume) as eluent. The eluent of the desired fraction was evaporated, yielding 9.6 parts (89.3%) of N-[4-[1-(1H-imidazol-1-yl)propyl]-2-nitrophenyl]-2-methylbenzeneacetamide; mp. 122° C. (interm. 48).

Workup

  1. stirringAfter stirring for 12 hours at room temperature
  2. extractionthe product was extracted with dichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe oily residue was purified by column chromatography over silica gel using
  7. additiona mixture of dichloromethane and methanol (98:2 by volume) as eluent
  8. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-680da90bcb32419a8a70a54614ecc6e7
Source dataset
uspto-grants-1992_09
Patent number
US05151421

Reaction notes

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