Dimethylformamide → N~2~-(2,6-Dimethylphenyl)glycinamide

HRID 2286595Notes

Reaction equation

HRID 2286595 reaction equation
CN(C)C=O.[CH3:6][C:7]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:8]=1[NH2:9].Cl[CH2:16][C:17]([NH2:19])=[O:18].C(=O)([O-])[O-].[K+].[K+]>O>[NH2:19][C:17]([CH2:16][NH:9][C:8]1[C:10]([CH3:14])=[CH:11][CH:12]=[CH:13][C:7]=1[CH3:6])=[O:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6580ChloroacetamideHCID 68962,6-DimethylanilineHCID 11430Potassium Carbonate

Product 1

HCID 15572228N~2~-(2,6-Dimethylphenyl)glycinamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 200 ml dimethylformamide to a mixture of 2,6-dimethylaniline (36.3 g, 0.30 mol), 2-chloroacetamide (74.8 g, 0.80 mol) and potassium carbonate (41.4 g, 0.3 mol). Heat at 120° for 72 hours, allow to cool, and pour into water. Extract with 1:1 ether-ethyl acetate. Wash the organic with 1.0 N HCl. Neutralize the aqueous layer with NaHCO3 and extract it with ethyl acetate. Dry, concentrate, and distill to collect a fraction, b.p. 157°-167°/0.1 mm. Recrystallize from methylene chloride-hexane to give as a solid, m.p. 91°-92°, N-aminocarbonylmethyl-2,6-dimethylaniline.

Workup

  1. temperatureHeat at 120° for 72 hours
  2. temperatureto cool
  3. extractionExtract with 1:1 ether-ethyl acetate
  4. washWash the organic with 1.0 N HCl
  5. extractionNeutralize the aqueous layer with NaHCO3 and extract it with ethyl acetate
  6. customDry
  7. concentrationconcentrate
  8. distillationdistill
  9. customto collect a fraction, b.p. 157°-167°/0.1 mm
  10. customRecrystallize from methylene chloride-hexane

Sources & evidence

ORD record
ord-26018b81ebad4a80a77140db28e5d745
Source dataset
uspto-grants-1981_05
Patent number
US04267193

Reaction notes

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