Phosgene → (1-Methylethyl)phenylcarbamic chloride

HRID 597479Notes

Reaction equation

HRID 597479 reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[C:11](Cl)([Cl:13])=[O:12]>C1C=CC=CC=1>[C:5]1([N:4]([CH:1]([CH3:3])[CH3:2])[C:11]([Cl:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 13032N-Isopropylaniline

Product 1

HCID 11446927(1-Methylethyl)phenylcarbamic chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of N-isopropylaniline (30 g) in dry benzene (150 ml) was cooled to 5°-10° C and phosgene passed therethrough slowly for 11/2 hours. The mixture was refluxed for 1 hour to remove excess phosgene, cooled and the amine hydrochloride was filtered off. The solvent was evaporated and the residue recrystallised from benzene-petroleum ether 1:1, giving 21.6 g, m.p. 89°-90° C.

Workup

  1. custom2 hours
  2. temperatureThe mixture was refluxed for 1 hour
  3. customto remove excess phosgene
  4. temperaturecooled
  5. filtrationthe amine hydrochloride was filtered off
  6. customThe solvent was evaporated
  7. customthe residue recrystallised from benzene-petroleum ether 1:1
  8. customgiving 21.6 g, m.p. 89°-90° C.

Sources & evidence

ORD record
ord-5a2d3794f42d45fb95a4328574b78042
Source dataset
uspto-grants-1977_03
Patent number
US04014862

Reaction notes

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