Hydrochloric Acid → N~2~-(Chloroacetyl)-N~2~-(2,6-dimethylphenyl)-N,N-dimethylglycinamide

HRID 436236Notes

Reaction equation

HRID 436236 reaction equation
[CH3:1][NH:2][C:3](=[O:14])[CH2:4][NH:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13].[CH3:15]N(C)C=O.[Cl:20][CH2:21][C:22](Cl)=[O:23].Cl>ClC1C=CC=CC=1>[CH3:1][N:2]([CH3:15])[C:3](=[O:14])[CH2:4][N:5]([C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])[C:22](=[O:23])[CH2:21][Cl:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6577Chloroacetyl chlorideHCID 542916472,6-Dimethylanilinoacetic acid methyl amide

Product 1

HCID 19758562N~2~-(Chloroacetyl)-N~2~-(2,6-dimethylphenyl)-N,N-dimethylglycinamide

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
110 °C

Procedure

31.4 g of 2,6-dimethylanilinoacetic acid methyl amide are dissolved in 250 ml of chlorobenzene. 1.5 ml of dimethyl formamide are added to this solution and the mixture is heated to 110° C. At this temperature 14.3 ml of chloroacetyl chloride are added dropwise with stirring. After 1 1/2 hours the evolution of HCl has virtually ceased. The reaction mixture is allowed to cool and concentrated in a rotary evaporator to leave as residue a blackish-brown oil which is crystallised from ethyl acetate with the addition of animal charcoal. Yield: 22.4 g of N-methyl-[N'-(2,6-dimethylphenyl)-N'-chloroacetylamino]-acetamide (m.p. 140° C-142° C). N,N-dimethyl-(N'-(2,6-dimethylphenyl)-N'-chloroacetylamino]-acetamide was obtained in analogous manner; m.p. 74°-76° C (from ether).

Workup

  1. customAfter 1 1/2 hours
  2. temperatureto cool
  3. concentrationconcentrated in a rotary evaporator
  4. customto leave as residue a blackish-brown oil which
  5. customis crystallised from ethyl acetate with the addition of animal charcoal

Sources & evidence

ORD record
ord-9f02ab4f862e4b77b1f6f6e8b0ef6249
Source dataset
uspto-grants-1977_02
Patent number
US04008066

Reaction notes

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