Diisopropylethylamine → 1-Cyclohexyl-2-isocyanatobenzene

HRID 1097823Notes

Reaction equation

HRID 1097823 reaction equation
[CH:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2C(O)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC[N:18]([CH:22](C)C)C(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1>C1(C)C=CC=CC=1>[CH:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[N:18]=[C:22]=[O:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 70205722-cyclohexylbenzoic Acid

Product 1

HCID 574747361-Cyclohexyl-2-isocyanatobenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-cyclohexylbenzoic acid (2 g, 9.8 mmol) and DIPEA (3.45 μL, 14.7 mmol) in toluene (25 mL) under nitrogen was added diphenylphosphoryl azide (2.1 mL, 9.8 mmol). The reaction mixture was stirred for 4 h at room temperature and then heated at 90° C. for 3 h. Upon cooling, the organic layer was washed with saturated ammonium chloride solution (2×10 mL) and brine (1×10 mL), dried (MgSO4), filtered and the solvent removed under reduced pressure to give the title compound as a clear amber oil.

Workup

  1. temperatureheated at 90° C. for 3 h
  2. temperatureUpon cooling
  3. washthe organic layer was washed with saturated ammonium chloride solution (2×10 mL) and brine (1×10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-f3fcec60ef7640e4b1e5822b980dbe1c
Source dataset
uspto-grants-2012_03
Patent number
US08143277B2

Reaction notes

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