Potassium Carbonate → N2-(2,4-dimethyl-6-nitrophenyl)-N1,N1-dimethylglycinamide

HRID 656411Notes

Reaction equation

HRID 656411 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH2:4].Cl[CH2:14][C:15]([N:17]([CH3:19])[CH3:18])=[O:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH:4][CH2:14][C:15]([N:17]([CH3:19])[CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 742196-Nitro-2,4-xylidineHCID 758862-chloro-N,N-dimethylacetamide

Product 1

HCID 68995353N2-(2,4-dimethyl-6-nitrophenyl)-N1,N1-dimethylglycinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2,4-dimethyl-6-nitroaniline (5.00 g, 30.1 mmol), 2-chloro-N,N-dimethylacetamide (18.3 g, 150 mmol), K2CO3 (6.24 g, 45.2 mmol), and KI (499 mg, 3.01 mmol) in DMF (100 mL) was heated at 120° C. for 7 h, then at 130° C. for 14 h. The cooled mixture was quenched with H2O (200 mL) and extracted with CH2Cl2 (3×150 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 50:50, to give the title compound. MS: m/z=252 (M+1).

Workup

  1. customThe cooled mixture was quenched with H2O (200 mL)
  2. extractionextracted with CH2Cl2 (3×150 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-1bf2d41d29504597a61766d24fd37ac7
Source dataset
uspto-grants-2011_12
Patent number
US08071771B2

Reaction notes

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