Dabco → 1-(4-Trimethylsilylphenyl)-3-(2,6-difluorobenzoyl)-urea

HRID 224764Notes

Reaction equation

[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[CH3:14][Si:15]([CH3:24])([CH3:23])[C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.C1N2CCN(CC2)C1>C1(C)C=CC=CC=1>[CH3:14][Si:15]([CH3:24])([CH3:23])[C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:7]([NH:6][C:4](=[O:5])[C:3]2[C:2]([F:1])=[CH:12][CH:11]=[CH:10][C:9]=2[F:13])=[O:8])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 6.0 g of 2,6-difluorobenzoylisocyanate in 20 ml of toluene was added dropwise at room temperature to a mixture of 5.4 g of 4-trimethylsilylaniline, 50 ml of toluene and 100 mg of Dabco®. The reaction mixture obtained was subsequently stirred at 60° C. for 3 hours. The reaction mixture was concentrated by evaporation, and the residue was recrystallised from acetone to obtain 1-(4-trimethylsilylphenyl)-3-(2,6-difluorobenzoyl)-urea of the formula ##STR8## as a white powder having a melting point of 187°-189° C.

Workup

customThe reaction mixture obtained
concentrationThe reaction mixture was concentrated by evaporation
customthe residue was recrystallised from acetone

Sources & evidence

ORD record: ord-a0baac8c2de44d3d9618b6b86aeb5c42
Source dataset: uspto-grants-1980_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04234573

Reaction notes

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