N,N'-Dimethylurea → 1,3-Dimethyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dione

HRID 1380437Notes

Reaction equation

HRID 1380437 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3](=[CH2:7])[C:4](O)=[O:5].[CH3:10][NH:11][C:12]([NH:14][CH3:15])=[O:13].C(OC(=O)C)(=O)C>>[CH3:10][N:11]1[CH2:7][CH:3]([C:2]([F:9])([F:8])[F:1])[C:4](=[O:5])[N:14]([CH3:15])[C:12]1=[O:13]

Participants

4

Reactant 3

HCID 7293N,N'-DimethylureaHCID 7918Acetic AnhydrideHCID 5876942-(Trifluoromethyl)acrylic acid

Product 1

HCID 130049781,3-Dimethyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dioneYield 85%

Conditions

Temperature
100 °C

Procedure

A mixture of α-trifluoromethylacrylic acid (4.31 g; 30.8 mmoles), 1,3-dimethylurea (2.75 g; 31.2 mmoles) and acetic anhydride (17 ml) was heated at 100° C. with stirring for one hour. The solvent was evaporated under reduced pressure, and the residue was purified by a column chromatography on silica gel (CHCl3) to give 5.50 g (yield: 84%) of 1,3-dimethyl-5-trifluoromethyldihydrouracil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by a column chromatography on silica gel (CHCl3)

Sources & evidence

ORD record
ord-f8b62e0e439e40ae9d3c558487234ef0
Source dataset
uspto-grants-1986_04
Patent number
US04581452

Reaction notes

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