Dimethylformamide dimethyl acetal → Methyl alpha-[(dimethylamino)methylene]-1H-1,2,3-triazole-1-acetate

HRID 241604Notes

Reaction equation

HRID 241604 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[N:9]1([C:14](=C)[C:15]([O:17][CH3:18])=[O:16])[CH:13]=[CH:12][N:11]=[N:10]1>>[CH3:6][N:4]([CH3:5])[CH:3]=[C:14]([N:9]1[CH:13]=[CH:12][N:11]=[N:10]1)[C:15]([O:17][CH3:18])=[O:16]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 69669790HCID 69669790, compound

Product 1

HCID 69669700Methyl alpha-[(dimethylamino)methylene]-1H-1,2,3-triazole-1-acetate

Conditions

Temperature
55 °C

Procedure

522 g of dimethylformamide dimethyl acetal were added to 400 g of methyl 2-(1H-1,2,3-triazol-1-yl)acrylate, and the mixture was heated to the boil. Low-boiling components formed were distilled off. After 4 h, the mixture was cooled to 55° C., and 1050 ml of methyl tert-butyl ether/2-propanol (3:1 v/v) were metered in. The resulting suspension was cooled to 22° C. and filtered. The filter cake was repeatedly washed with methyl tert-butyl ether and dried under reduced pressure at 40° C. This gave 493 g of the title compound as a solid.

Workup

  1. temperaturethe mixture was heated to the boil
  2. customLow-boiling components formed
  3. distillationwere distilled off
  4. temperatureThe resulting suspension was cooled to 22° C.
  5. filtrationfiltered
  6. washThe filter cake was repeatedly washed with methyl tert-butyl ether
  7. customdried under reduced pressure at 40° C

Sources & evidence

ORD record
ord-075b37b3fcd445aabe31a1f217242541
Source dataset
uspto-grants-2014_02
Patent number
US08653074B2

Reaction notes

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