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

HRID 1090460
Notes
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Reaction equation

HRID 1090460 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 1181687611-Dodecen-1-ol, 12,12-difluoro-

Product 1

HCID 1991537112,12-difluoro-11-dodecenyl N-phenylcarbamateYield 80%

Reagents, catalysts & solvents 2

HCID 9798523Di-n-butyl diacetoxy tinCatalystHCID 8900HeptaneSolvent

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

  1. additionUpon completion of addition
  2. temperatureto cool to ambient temperature where it
  3. stirringstirred for 18 hours
  4. temperatureAfter this time the reaction mixture was cooled in a freezer
  5. filtrationa precipitate was collected by filtration
  6. washThe filter cake was washed with cold pentane
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes