Nitrogen → 4-Methylphenyl isocyanate

HRID 2210285Notes

Reaction equation

HRID 2210285 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([N:7](C)[C:8](OCC)=[O:9])=[CH:3][CH:2]=1.B.N#N>C(N(CC)CC)C>[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([N:7]=[C:8]=[O:9])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 6331BoraneHCID 23535589HCID 23535589, compound

Product 1

HCID 693254-Methylphenyl isocyanate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Ethylene glycol was reacted with boron trichloride to form the borane compound of formula ##STR32## (For detailed procedure see Genmarie et. al., Tetrahedron Letters, 1984, 25, 2279). To a solution of p-tolyl methyl urethane there were added the borane compound and triethylamine and the mixture was refluxed for 5 minutes (N2 atmosphere). An instantaneous reaction was observed and a white cloudy suspension appeared in the reaction flask, due to the formation of Et3NH+Cl-. p-Tolyl isocyanate was obtained and IR spectra showed the complete disappearance of urethane moieties and the formation of isocyanate moieties.

Workup

  1. customAn instantaneous reaction

Sources & evidence

ORD record
ord-7e08c5c283124123bb8b97e07ae26831
Source dataset
uspto-grants-1995_10
Patent number
US05457229

Reaction notes

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