Phenyl isocyanate → Formanilide

HRID 1703980Notes

Reaction equation

HRID 1703980 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>O1CCOCC1.C(N(CC)CC)C>[CH:8]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:9]

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 7671FormanilideYield 98%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of phenyl isocyanate (1.2 g.; 0.01 mole in 100 ml. anhydrous 1,4-dioxane containing two drops of anhydrous triethylamine was mixed with 500 mg. of 10% Pd-on-carbon and shaken at a pressure of 50 p.s.i. of hydrogen on a Parr low pressure hydrogenator. The uptake of hydrogen was complete in 5 minutes. The catalyst was collected and washed with 50 ml. of 1,4-dioxane. The solvent was evaporated to give 1.2 g. (98% yield) of slightly yellow oil which slowly crystallized. The product was confirmed to be formanilide by ir, nmr and glc analyses.

Workup

  1. customThe catalyst was collected
  2. washwashed with 50 ml
  3. customThe solvent was evaporated
  4. customto give 1.2 g
  5. custom(98% yield) of slightly yellow oil which slowly crystallized

Sources & evidence

ORD record
ord-2d45971b8e3b45daa99d054cf91dede9
Source dataset
uspto-grants-1978_11
Patent number
US04125724

Reaction notes

Loading…