6-Nitro-2,4-xylidine → N2-(2,4-dimethyl-6-nitrophenyl)-N1,N1-dimethylglycinamide

HRID 656833Notes

Reaction equation

HRID 656833 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]>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

4

Reactant 2

HCID 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), K2 CO3 (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 CH2 Cl2 (3×150 mL). The combined organic layers were dried over Na2 SO4, 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 CH2 Cl2 (3×150 mL)
  3. customThe combined organic layers were dried over Na2 SO4
  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-3a9019342f324f8783a9397697e7196a
Source dataset
uspto-grants-2011_12
Patent number
US08071772B2

Reaction notes

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