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

HRID 2184513Notes

Reaction equation

HRID 2184513 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]ethanone

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 or 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. ANALYSIS: Calculated for C13H18ClNO3: 57.89%C 5.98%H 5.19%N Found: 57.08%C 5.85%H 5.13%N

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-a5887169149547a096a2dea32cd58a3f
Source dataset
uspto-grants-2002_06
Patent number
USRE037729E1

Reaction notes

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