Dimethylformamide dimethyl acetal → methyl N-[[2-chloro-5-[3-(dimethylamino)-1-oxo-2-propen-1-yl]phenyl]methyl]carbamate

HRID 1408428Notes

Reaction equation

HRID 1408428 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([Cl:16])=[C:8]([CH2:10][NH:11][C:12](=[O:15])[O:13][CH3:14])[CH:9]=1)(=[O:3])[CH3:2].CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>C1(C)C=CC=CC=1>[Cl:16][C:7]1[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH:2]=[CH:19][N:20]([CH3:22])[CH3:21])=[CH:9][C:8]=1[CH2:10][NH:11][C:12](=[O:15])[O:13][CH3:14]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 12151316HCID 12151316, compound

Product 1

HCID 66789975methyl N-[[2-chloro-5-[3-(dimethylamino)-1-oxo-2-propen-1-yl]phenyl]methyl]carbamateYield 81.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
135 °C

Procedure

To a solution of methyl N-[(5-acetyl-2-chlorophenyl)methyl]carbamate (10 g, 41.5 mmol) (prepared by the method given in European Patent Publication EP 1586552) in toluene was added N,N-dimethylformamide dimethyl acetal (9.88 g, 82.9 mmol) and the reaction mixture was heated at 135° C. for 2 days. TLC analysis (50% ethyl acetate/pet ether) showed the reaction was complete. The solvent was evaporated under vacuum and water was added to the residue. The water layer was extracted with ethyl acetate three times. The combined the organic phases were washed with water, brine, dried over Na2SO4 and concentrated under vacuum to give the title compound (10 g, 81% yield) as solid.

Workup

  1. customThe solvent was evaporated under vacuum and water
  2. additionwas added to the residue
  3. extractionThe water layer was extracted with ethyl acetate three times
  4. washwere washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-fe5b4cdd22514db1a74c1fd62e83e454
Source dataset
uspto-grants-2014_12
Patent number
US08921360B2

Reaction notes

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