Phenyl isocyanate → 12,12-difluoro-11-dodecenyl N-phenylcarbamate

HRID 1090460Notes

Reaction equation

[F:1][C:2]([F:15])=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].[C:16]1([N:22]=[C:23]=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCCCCCC.C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC>[C:16]1([NH:22][C:23](=[O:24])[O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[C:2]([F:15])[F:1])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 2.0 grams (0.0091 mole) of 12,12-difluoro-11-dodecen-1-ol (prepared in Example 5) in 15 ml of heptane was added two drops of dibutyltin diacetate, and then 1.2 grams (0.0100 mole) of phenyl isocyanate was added dropwise. Upon completion of addition, the reaction mixture was warmed to 80° C. where it stirred for 30 minutes. The reaction mixture was allowed to cool to ambient temperature where it stirred for 18 hours. After this time the reaction mixture was cooled in a freezer, and a precipitate was collected by filtration. The filter cake was washed with cold pentane and dried yielding 2.47 grams of 12,12-difluoro-11-dodecenyl N-phenylcarbamate; m.p. 54°-56° C. The nmr spectrum was consistent with the proposed structure.

Workup

additionUpon completion of addition
temperatureto cool to ambient temperature where it
stirringstirred for 18 hours
temperatureAfter this time the reaction mixture was cooled in a freezer
filtrationa precipitate was collected by filtration
washThe filter cake was washed with cold pentane
customdried

Sources & evidence

ORD record: ord-d7716cdc07b7495ab782c02dc74df158
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05081287

Reaction notes

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