HCID 20747587, compound → HCID 58091579, compound

HRID 1873997Notes

Reaction equation

HRID 1873997 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]>COC(OC)N(C)C>[CH3:8][N:10]([CH3:12])/[CH:11]=[CH:2]/[C:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([N:10]([CH3:11])[CH3:12])=[O:9])=[CH:6][CH:5]=1)=[O:3]

Participants

3

Reactant 1

HCID 20747587HCID 20747587, compound

Product 1

HCID 58091579HCID 58091579, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

A mixture of crude 4-acetyl-N,N-dimethylbenzamide (24.0 g) and N,N-dimethylformamide dimethyl acetal (100 mL) was heated to reflux for 15 h, cooled to room temperature and concentrated. The residue was washed with ether and dried under vacuum to provide (E)-4-(3-(dimethylamino)acryloyl)-N,N-dimethylbenzamide as brown solid (16 g, 27% yield over 2 steps). MS (ES+) m/z: 247 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 15 h
  3. concentrationconcentrated
  4. washThe residue was washed with ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-36b070ad4fd94e7088bdaed011eeee4b
Source dataset
uspto-grants-2012_11
Patent number
US08304539B2

Reaction notes

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