Hydrogen Bromide → HCID 23326949, compound

HRID 1380411Notes

Reaction equation

HRID 1380411 reaction equation
[F:1][C:2]([F:12])([F:11])[CH:3]1[CH2:8]NC(=O)[NH:5][C:4]1=[O:10].FC(F)(F)C(=O)C.[BrH:20]>CO>[Br:20][CH2:8][CH:3]([C:2]([F:12])([F:11])[F:1])[C:4]([NH2:5])=[O:10]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 56385-(Trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dioneHCID 9871Methyl trifluoromethyl ketone

Product 1

HCID 23326949HCID 23326949, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

One conventional method for synthesizing 5-trifluoromethyldihydrouracil comprises converting trifluoroacetone to cyanohydrin, acetylating the product, heat-decomposing the acetylated product, reacting the resulting alpha-trifluoroacrylonitrile with hydrogen bromide in methanol to form beta-bromo-alpha-trifluoromethylpropionamide, reacting the amide with urea or acetylurea, and cyclizing the resulting compound in hydrochloric acid [C. Heidelberger, D. G. Parsons and D. C. Remy, J. Med. Chem., 7, 1 (1964)].

Workup

  1. temperatureheat-decomposing the acetylated product

Sources & evidence

ORD record
ord-2de6f4c489814505ab45a2b94c62795b
Source dataset
uspto-grants-1986_04
Patent number
US04581452

Reaction notes

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