Dimethylformamide dimethyl acetal → 2-Acetylamino-5-((E)-3-dimethylamino-acryloyl)-4-trifluoromethyl-benzoic acid methyl ester

HRID 906581Notes

Reaction equation

HRID 906581 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH:17][C:18](=[O:20])[CH3:19].CO[CH:24](OC)[N:25]([CH3:27])[CH3:26]>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])/[CH:11]=[CH:24]/[N:25]([CH3:27])[CH3:26])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH:17][C:18](=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 591644065-Acetyl-2-acetylamino-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 591644242-Acetylamino-5-((E)-3-dimethylamino-acryloyl)-4-trifluoromethyl-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-acetyl-2-acetylamino-4-trifluoromethyl-benzoic acid methyl ester (2.46 g, 8.1 mmol) and N,N dimethyl formamide dimethyl acetal (1.1 mL, 8.1 mmol) was stirred at 90° C. for 4 h. The mixture was diluted with AcOEt. The organic phase was washed with water, dried (Na2SO4) and concentrated in vacuo to afford a yellow paste. The crude product was purified by flash chromatography (silica gel, EtOAc/hexanes (50:50 to 100:0)) to provide the title compound as a beige paste (1.12 g, 39%). ES-MS: m/z 359.3 [M+H]+, rt 4.77 min.

Workup

  1. washThe organic phase was washed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customto afford a yellow paste
  5. customThe crude product was purified by flash chromatography (silica gel, EtOAc/hexanes (50:50 to 100:0))

Sources & evidence

ORD record
ord-d8341f6f12af420aa91306e10f882c34
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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