Benzene → 1-Methyl-1-phenyl-ethylisocyanate

HRID 1808734Notes

Reaction equation

HRID 1808734 reaction equation
C1C=CC=CC=1.[C:7]([NH2:16])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:9])[CH3:8].C(N(CC)CC)C.[C:24](Cl)(Cl)=[O:25]>C(OCC)C.C1(C)C=CC=CC=1>[N:16]([C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:9])[CH3:8])=[C:24]=[O:25]

Participants

7

Reactant 4

HCID 241BenzeneHCID 6371PhosgeneHCID 8471TriethylamineHCID 68509Cumylamine

Product 1

HCID 27694301-Methyl-1-phenyl-ethylisocyanate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

To a benzene (2 mL) solution of cumylamine (1.80 g, 13.3 mmol) and triethylamine (1.86 mL, 13.3 mmol) was added a 20% toluene solution of phosgene (17.5 mL, 33.3 mmol) dropwise. After completion, the reaction mixture was heated to 60° C. for 2 hours. It was then cooled to room temperature, charged with diethyl ether (20 mL), and filtered. Concentration of the filtrate in vacuo afforded the title compound. This crude product was used in the subsequent step without further purification.

Workup

  1. temperatureIt was then cooled to room temperature
  2. filtrationfiltered

Sources & evidence

ORD record
ord-fe3dccab2b714d998f38ddba15056b2c
Source dataset
uspto-grants-2013_01
Patent number
US08361994B2

Reaction notes

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