Ethanol → Ethyl N-phenylcarbamate

HRID 1731422Notes

Reaction equation

HRID 1731422 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+]([C:11]1[CH:16]=CC=CC=1)([O-])=O.IC(I)(I)I.[OH-:22].[Rb+].[C]=O.[CH2:26]([OH:28])C>[Pd](Cl)Cl>[C:2]1([NH:1][C:26](=[O:28])[O:22][CH2:16][CH3:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 6

HCID 702EthanolHCID 6115Aniline2×HCID 7416Nitrobenzene2×HCID 10487Methane, tetraiodo-HCID 62393Rubidium hydroxide (Rb(OH))HCID 178418416HCID 178418416, compound2×

Product 1

HCID 7591Ethyl N-phenylcarbamate

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Procedure

In a 200 ml stirring type autoclave were charged 30 mmols of aniline, 15 mmols of nitrobenzene, 50 ml of ethanol, 3 mmols of palladium chloride, 3 mmols of tetraiodomethane and 3 mmols of rubidium hydroxide. After the air inside the autoclave had been replaced with carbon monoxide, carbon monoxide was pressurized into the autoclave to 120 Kg/cm2, and the reaction was carried out at 180° C. for 5 hours with stirring. As the result of analysis of the reaction solution, the conversions of aniline and nitrobenzene were 21% and 29%, respectively, and 8 mmols of ethyl N-phenylcarbamate were obtained.

Workup

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

Sources & evidence

ORD record
ord-fa798d41ff08449c9a5db5ad96fd995c
Source dataset
uspto-grants-1986_11
Patent number
US04621149

Reaction notes

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