Phenyl isocyanate → HCID 1377176, compound

HRID 426659Notes

Reaction equation

HRID 426659 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[NH:2][NH2:3].[C:7]1([N:13]=[C:14]=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1C=CC=CC=1>[C:7]1([NH:13][C:14]([NH:3][NH:2][C:1]([O:5][CH3:6])=[O:4])=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 80519Methyl carbazate

Product 1

HCID 1377176HCID 1377176, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of methyl carbazate (91.9 g, 1.02 moles) in 450 ml of benzene was added dropwise with stirring during 45 min. to phenyl isocyanate (122 g. 1.02 moles); a temperature rise to near 80° C. was observed. After addition of the ester solution the mixture was heated under reflux, with stirring, for 45 min. Stirring was continued at ambient temperature for 15 hr. Removal of volatiles under reduced pressure gave 210.6 g (99%) of product ester, as long prisms, m.p. 154°-155°. Recrystallization from isopropyl alcohol/ethanol (4/1) gave a polymorph as chunky crystals, m.p. 166°-168°.

Workup

  1. customto near 80° C.
  2. temperaturewas heated
  3. temperatureunder reflux
  4. stirringStirring
  5. waitwas continued at ambient temperature for 15 hr
  6. customRemoval of volatiles under reduced pressure

Sources & evidence

ORD record
ord-9c04d2033aee42a3bf7cf0b8db9f55e1
Source dataset
uspto-grants-1979_10
Patent number
US04170706

Reaction notes

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