Phenyl isocyanate → HCID 1377176, compound

HRID 1703990Notes

Reaction equation

HRID 1703990 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-b2429c93a2af4d6d850c5b902bcb3844
Source dataset
uspto-grants-1978_11
Patent number
US04125728

Reaction notes

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