Urea → 5-(Heptafluoropropyl)dihydropyrimidine-2,4(1H,3H)-dione

HRID 1380434Notes

Reaction equation

HRID 1380434 reaction equation
[F:1][C:2]([F:15])([C:11]([F:14])([F:13])[F:12])[C:3]([F:10])([F:9])[C:4](=[CH2:8])[C:5](O)=[O:6].[NH2:16][C:17]([NH2:19])=[O:18].C(OC(=O)C)(=O)C>C(O)C>[F:1][C:2]([F:15])([C:11]([F:14])([F:13])[F:12])[C:3]([F:10])([F:9])[CH:4]1[CH2:8][NH:19][C:17](=[O:18])[NH:16][C:5]1=[O:6]

Participants

5

Reactant 3

HCID 1176UreaHCID 7918Acetic AnhydrideHCID 21277491HCID 21277491, compound

Product 1

HCID 134576425-(Heptafluoropropyl)dihydropyrimidine-2,4(1H,3H)-dioneYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of α-heptafluoropropylacrylic acid (240 mg; 1.0 mmole), urea (64 mg; 1.1 mmoles) and acetic anhydride (0.6 ml) was heated at 100° C. with stirring for 40 minutes. Then, ethanol (3 ml) was added to the reaction mixture to give 180 mg (yield: 64%) of 5-heptafluoropropyldihydrouracil as colorless crystals. m.p.: 223°-224 (decomp.).

Sources & evidence

ORD record
ord-9eb026844fda4258b6f30257cbd6f2de
Source dataset
uspto-grants-1986_04
Patent number
US04581452

Reaction notes

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