1,2-Dichloroethane → 2-(4-Fluorophenyl)-N-methoxy-N-methylacetamide

HRID 2245235Notes

Reaction equation

HRID 2245235 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH3:12][NH:13][O:14][CH3:15].C(N(CC)CC)C.C(Cl)CCl>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:13]([O:14][CH3:15])[CH3:12])=[O:11])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 98372-(4-Fluorophenyl)acetic acidHCID 14232N,O-Dimethylhydroxylamine

Product 1

HCID 210993112-(4-Fluorophenyl)-N-methoxy-N-methylacetamideYield 98.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 16.7 g (108.4 mmol) (4-fluorophenyl)acetic acid in dry methylene chloride under nitrogen atmosphere was added 13.8 g (141.5 mmol) N,O-dimethyl-hydroxylamine, 20 mL triethylamine, 14.2 g (119.3 mmol) 4-dimethylaminopyridine (DMAP) and 27 g (140.6 mmol) EDC. The reaction mixture was stirred at RT for 2 hr then transferred to a separatory funnel. The mixture was washed consecutively with 2 N aq. HCl, brine, saturated aq. NaHCO3 and brine. The organic layer was dried over drying agent, 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: 7.26 (2H, m), 7.02 (2H, m), 3.77 (2H, s), 3.65 (3H, s), 3.21 (3H, s).

Workup

  1. customthen transferred to a separatory funnel
  2. washThe mixture was washed consecutively with 2 N aq. HCl, brine, saturated aq. NaHCO3 and brine
  3. customThe organic layer was dried
  4. customover drying agent
  5. filtrationfiltered
  6. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-9de6345d87df4176a3bbd21238ab9feb
Source dataset
uspto-grants-2010_03
Patent number
US07683068B2

Reaction notes

Loading…