Phenylurea → HCID 13313793, compound

HRID 1380435Notes

Reaction equation

[F:1][C:2]([F:9])([F:8])[C:3](=[CH2:7])[C:4](O)=[O:5].[C:10]1([NH:16][C:17]([NH2:19])=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OC(=O)C)(=O)C>>[C:10]1([N:16]2[C:4](=[O:5])[CH:3]([C:2]([F:9])([F:8])[F:1])[CH2:7][NH:19][C:17]2=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Reactant 3

HCID 6145Phenylurea

HCID 7918Acetic Anhydride

HCID 5876942-(Trifluoromethyl)acrylic acid

Product 1

HCID 13313793HCID 13313793, compoundYield 46.2%

Conditions

Temperature: 100 °C

Procedure

A mixture of α-trifluoromethylacrylic acid (350 mg; 2.5 mmoles), phenylurea (353 mg; 2.6 mmoles) and acetic anhydride (2 ml) was heated at 100° C. with stirring for 1 hour. After cooling, the precipitated solid was collected by filtration to give 298 mg (yield: 46%) of 3-phenyl-5-trifluoromethyldihydrouracil. The solvent was evaporated from the filtrate, and the residue was recrystallized from chloroform/hexane to give additional 133 mg (yield: 21%) of the above product. The total yield was 67%. The physical and spectral properties of the resulting 3-phenyl-5-trifluoromethyldihydrouracil completely agreed with those of the product obtained in Example 11.

Workup

temperatureAfter cooling
filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record: ord-93081b4baba74af6aeab6089095dfd80
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04581452

Reaction notes

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