1-Bromo-3-chloropropane → 1-[3-Acetylamino-4-(3-chloropropoxy)phenyl]ethanone

HRID 742675Notes

Reaction equation

HRID 742675 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=[CH:9][C:10]=1[OH:11])(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Cl:21][CH2:22][CH2:23][CH2:24]Br>CC(C)=O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=[CH:9][C:10]=1[O:11][CH2:24][CH2:23][CH2:22][Cl:21])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 283886N-(5-Acetyl-2-hydroxyphenyl)ethanimidic acid

Product 1

HCID 100159331-[3-Acetylamino-4-(3-chloropropoxy)phenyl]ethanoneYield 78.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 1-[3-acetylamino-4-hydroxyphenyl] ethanone (7.7 g, 40 mmol), K2CO3 (5.7 g), 3-chloro-1-bromopropane (8.9 g, 56 mmol) and acetone (100 ml) was refluxed for 16 hours. The reaction was allowed to cool to ambient temperature and filtered. Concentration of the filtrate yielded 8.5 g of a white solid. The solid was recrystallized from toluene and then from ethanol to afford 6.5 g of an off-white solid. A 3.3 g sample of this material was flash chromatographed on silica gel with ethyl acetate as eluent. Concentration of the appropriate fractions afforded 2.8 g of a solid. The solid was recrystallized from toluene and then from ethanol-water to yield 2.2 g (51%) of a solid, m.p.=124°-126° C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. filtrationfiltered

Sources & evidence

ORD record
ord-b0db47b04b974505ace4403b5256fa61
Source dataset
uspto-grants-1996_09
Patent number
US05554614

Reaction notes

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