Methylurea → 1-(2-Hydroxycarbonyl-3,3,3-trifluoropropyl)-3-methylurea

HRID 1380418Notes

Reaction equation

HRID 1380418 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3](=[CH2:7])[C:4]([OH:6])=[O:5].[CH3:10][NH:11][C:12]([NH2:14])=[O:13]>CN(C=O)C>[CH3:10][N:11]1[CH2:7][CH:3]([C:2]([F:9])([F:8])[F:1])[C:4](=[O:5])[NH:14][C:12]1=[O:13].[CH3:10][N:11]1[C:4](=[O:5])[CH:3]([C:2]([F:9])([F:8])[F:1])[CH2:7][NH:14][C:12]1=[O:13].[OH:5][C:4]([CH:3]([C:2]([F:9])([F:8])[F:1])[CH2:7][NH:14][C:12]([NH:11][CH3:10])=[O:13])=[O:6]

Participants

6

Reactant 2

HCID 11719MethylureaHCID 5876942-(Trifluoromethyl)acrylic acid

Product 3

HCID 130049793-Methyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dioneYield 2%HCID 130049801-Methyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dioneYield 12%HCID 133137911-(2-Hydroxycarbonyl-3,3,3-trifluoropropyl)-3-methylureaYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of α-trifluoromethylacrylic acid (700 mg; 5.0 mmoles) and methylurea (407 mg; 5.5 mmoles) in DMF (3 ml) was heated at 90° C. with stirring for 4 hours. DMF was evaporated under reduced pressure. The residue was purified by a column chromatography on silica gel to give 118 mg (yield 12%) of 1-methyl-5-trifluoromethyl-5,6-dihydrouracil (OF-3), 20 mg (yield: 2%) of 3-methyl-5-trifluoromethyl-5,6-dihydrouracil and 706 mg (yield: 66%) of 1-(2-hydroxycarbonyl-3,3,3-trifluoropropyl)-3-methylurea.

Workup

  1. customDMF was evaporated under reduced pressure
  2. customThe residue was purified by a column chromatography on silica gel

Sources & evidence

ORD record
ord-6d52da10ebb04d9395ae634335291e35
Source dataset
uspto-grants-1986_04
Patent number
US04581452

Reaction notes

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