Carbamate → 1-Methyl-3-phenylurea

HRID 1112602Notes

Reaction equation

HRID 1112602 reaction equation
CNC(=O)O[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C1(O)C=CC=CC=1.C(=O)([O-])N.CN=C=O.[C:27]([O-])(=O)[NH:28][C:29]([NH2:31])=[O:30].NC1C=CC=CC=1>>[CH3:27][NH:28][C:29]([NH:31][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:30]

Participants

7

Reactant 6

HCID 276CarbamateHCID 996Phenol5×HCID 6115AnilineHCID 12228Methyl Isocyanate2×HCID 16034Phenyl MethylcarbamateHCID 9543250Allophanate

Product 1

HCID 138801-Methyl-3-phenylurea

Procedure

Following pyrolysis the residual material in the flask had a composition of 25 mole percent phenyl N-methylcarbamate and 75 mole percent phenol. The flask was cooled, a vacuum applied and phenol was stripped at a pressure of 20 mm Hg. Recovered phenol was also chromatographically pure. The residual carbamate remaining after phenol was stripped was returned to the pyrolysis flask. After 3 cycles of pyrolysis and phenol stripping, analysis showed: 96% conversion to methyl isocyanate, 2% unconverted material and 2% conversion to the allophanate. The methyl isocyanate was identified by reaction with aniline to give 1-methyl-3-phenylurea melting at 149°-150.5° C.

Workup

  1. temperatureThe flask was cooled

Sources & evidence

ORD record
ord-0f75f04c64664afbb9dd5b38d75adc43
Source dataset
uspto-grants-1978_10
Patent number
US04123450

Reaction notes

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