Chloroacetyl chloride → 3-(N-chloroacetyl-2,6-dimethylphenylamino)-2-butanone

HRID 443340Notes

Reaction equation

HRID 443340 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[NH:14][CH:15]([CH3:19])[C:16](=[O:18])[CH3:17]>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]([N:14]([C:8]1[C:9]([CH3:13])=[CH:10][CH:11]=[CH:12][C:7]=1[CH3:6])[CH:15]([CH3:19])[C:16](=[O:18])[CH3:17])=[O:4]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 124914753-(2,6-Dimethylphenylamino)-2-butanone

Product 1

HCID 124914823-(N-chloroacetyl-2,6-dimethylphenylamino)-2-butanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 152.6-g (1.35-mol) sample of chloroacetyl chloride was added over 0.25 hour in small portions to a stirred solution of 170.8 g (0.89 mol) 3-(2,6-dimethylphenylamino)-2-butanone in 500 ml toluene. The reaction mixture was heated under reflux for 3 hours, cooled and filtered. The filtrate was concentrated and chromatographed on silica gel using dichloromethane eluant. The eluted material was recrystallized several times from ethyl ether/hexane to give the 3-(N-chloroacetyl-2,6-dimethylphenylamino)-2-butanone product, as a brown solid, m.p. 78°-82° C. The infrared spectrum of the product showed strong carbonyl absorption at 5.8 and 6.1 microns. This product is tabulated in Table I as Compound No. 5-A.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customchromatographed on silica gel
  7. customThe eluted material was recrystallized several times from ethyl ether/hexane

Sources & evidence

ORD record
ord-b0069523825c47fd90c650995a05c402
Source dataset
uspto-grants-1981_04
Patent number
US04260410

Reaction notes

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