Dimethylformamide dimethyl acetal → 3-Dimethylamino-1-(2'-methoxy-5'-acetamidophenyl)prop-2-en-1-one

HRID 1159494Notes

Reaction equation

HRID 1159494 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:20])[CH3:19])=[CH:13][C:12]=1[C:21](=[O:23])[CH3:22]>C(O)C>[CH3:6][N:4]([CH3:5])[CH:3]=[CH:22][C:21]([C:12]1[CH:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[CH:15]=[CH:16][C:11]=1[O:10][CH3:9])=[O:23]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetal3×HCID 28174183-Acetyl-4-methoxyacetanilide

Product 1

HCID 666034303-Dimethylamino-1-(2'-methoxy-5'-acetamidophenyl)prop-2-en-1-oneYield 101.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
22 °C

Procedure

Dimethylformamide dimethyl acetal (693.3 g) was added to a suspension of 2′-methoxy-5′-acetamidoacetophenone (3, 1215.1 g) in ethanol (12.15 L) stirred under nitrogen at 22° C. After the resulting suspension had been stirred and refluxed under nitrogen for 18 hours, all solids had dissolved, and additional dimethylformamide dimethyl acetal (346.2 g) was added to the homogeneous reaction mixture. Stirring and refluxing under nitrogen were continued for an additional 30 hours, after which additional dimethylformamide dimethyl acetal (346.2 g) was added. The reaction mixture was then stirred and refluxed under nitrogen for a final 17.5 hours, after which the reaction mixture was rotary evaporated at <45° C. and <50 mm HgA to a solid residue that was dried further overnight at <45° C. and <1 mm HgA to provide brown solid 4 (1547.9 g, 100.6% yield). LC/MS analyses revealed 98.3% and 100% conversion of 3 to 4 before and after evaporation of solvent, respectively.

Workup

  1. stirringAfter the resulting suspension had been stirred
  2. temperaturerefluxed under nitrogen for 18 hours
  3. dissolutionall solids had dissolved
  4. stirringStirring
  5. temperaturerefluxing under nitrogen
  6. stirringThe reaction mixture was then stirred
  7. temperaturerefluxed under nitrogen for a final 17.5 hours
  8. customafter which the reaction mixture was rotary evaporated at <45° C.
  9. custom<50 mm HgA to a solid residue that was dried further overnight at <45° C.

Sources & evidence

ORD record
ord-662f99a291d04c5db5a170b694992c61
Source dataset
uspto-grants-2010_10
Patent number
US07812176B2

Reaction notes

Loading…