Methanol → Methyl phenylcarbamate

HRID 1731424Notes

Reaction equation

HRID 1731424 reaction equation
C1(N[C:8](NC2C=CC=CC=2)=[O:9])C=CC=CC=1.[N+:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([O-])=O.[I-].[Cs+].[C]=O.[CH3:30][OH:31]>[Pd](Cl)Cl>[C:20]1([NH:17][C:8](=[O:9])[O:31][CH3:30])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 7416Nitrobenzene2×HCID 7595Carbanilide2×HCID 24601Cesium iodideHCID 178418416HCID 178418416, compound2×

Product 1

HCID 17451Methyl phenylcarbamate

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Procedure

In a 200 ml stirring type autoclave were charged 30 mmols of N,N'-diphenylurea, 15 mmols of nitrobenzene, 50 ml of methanol, 0.5 mmol of palladium chloride and 5 mmols of cesium iodide. After the air inside the autoclave had been replaced with carbon monoxide, carbon monooxide was pressurized into the autoclave to 120 Kg/cm2, and the reaction was carried out at 180° C. for 4 hours with stirring. As the result of analysis of the reaction solution obtained, the conversions of N,N'-diphenylurea and nitrobenzene were 25% and 30%, respectively, and 14 mmols of methyl N-phenylcarbamate were obtained.

Workup

  1. stirringwith stirring
  2. customAs the result of analysis of the reaction solution
  3. customobtained

Sources & evidence

ORD record
ord-ea4cd2b658564101a34232aacf70050b
Source dataset
uspto-grants-1986_11
Patent number
US04621149

Reaction notes

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