Dimethylformamide dimethyl acetal → N-[1-Dimethylaminomethylidene]-3-methylsulfanylbenzamide

HRID 657524Notes

Reaction equation

HRID 657524 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH2:8])=[O:7].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>CO>[CH3:14][N:15]([CH3:17])[CH:16]=[N:8][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][CH:11]=[C:3]([S:2][CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 445812973-Methylsulfanylbenzamide

Product 1

HCID 59442543N-[1-Dimethylaminomethylidene]-3-methylsulfanylbenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.5 g of 3-methylsulfanylbenzamide and 18 ml of dimethylformamide dimethyl acetal were heated at 120° C. while the formed methanol was eliminated by distillation. After heating for 3 h, the volatiles were removed in vacuo. The crude product was purified by flash chromatography (300 g silica gel; DCM/MOH, gradient from 100:0 to 95:5). 8 g of the title compound were obtained as an oil.

Workup

  1. distillationwas eliminated by distillation
  2. temperatureAfter heating for 3 h
  3. customthe volatiles were removed in vacuo
  4. customThe crude product was purified by flash chromatography (300 g silica gel; DCM/MOH, gradient from 100:0 to 95:5)

Sources & evidence

ORD record
ord-af8e0a68413e4818b933fa093ce5b3de
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

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