1,2-Dichloroethane → N-Methoxy-N-methyl-2-(2-methylphenyl)acetamide

HRID 1644773Notes

Reaction equation

HRID 1644773 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.C(Cl)Cl.[CH3:15][NH:16][O:17][CH3:18].C(N(CC)CC)C.C(Cl)CCl>CN(C)C1C=CN=CC=1>[CH3:18][O:17][N:16]([CH3:15])[C:9](=[O:11])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6344DichloromethaneHCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 69519o-Tolylacetic acid

Product 1

HCID 21099310N-Methoxy-N-methyl-2-(2-methylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of (2-methylphenyl)acetic acid in dry methylene chloride (16.7 g, 108.4 mmol) under nitrogen atmosphere was added N,O-dimethylhydroxylamine (13.8 g, 141.5 mmol), triethylamine (20 mL, 143.8 mmol), 4-dimethylaminopyridine (DMAP, 14.2 g, 119.3 mmol) and EDC (27 g, 140.6 mmol). The reaction mixture was stirred at RT for 2 hr then transferred to a separation funnel. The mixture was washed consecutively with 2 N aq. HCl, brine, saturated aq. NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and the solvent evaporated under vacuum to give 21 g of the crude title compound which was used without further purification. 1H-NMR (CDCl3): δ: 7.20 (4H, m), 3.80 (2H, s), 3.65 (2H, s), 3.65 (3H, s), 2.34 (3H, m).

Workup

  1. customthen transferred to a separation funnel
  2. washThe mixture was washed consecutively with 2 N aq. HCl, brine, saturated aq. NaHCO3 and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-f127a1b0db8b444db52b7c6406df1604
Source dataset
uspto-grants-2012_02
Patent number
US08124633B2

Reaction notes

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