Phosgene → 3,4,5-Trichlorophenylisocyanate

HRID 5854Notes

Reaction equation

HRID 5854 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:10])[C:8]=1[Cl:9])[NH2:5].[C:11](Cl)(Cl)=[O:12]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:5]=[C:11]=[O:12])[CH:6]=[C:7]([Cl:10])[C:8]=1[Cl:9]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 124693,4,5-Trichloroaniline

Product 1

HCID 145450443,4,5-Trichlorophenylisocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3,4,5-trichloroaniline (400 mg; 2 mmol) in toluene (15 ml) and phosgene (6 ml 20% in toluene; 12 mmol) was refluxed for 6 h. The solvent was removed under reduced pressure to give crude 3,4,5-trichlorophenylisocyanate. To the crude product was added 3-[4-(4-chlorophenyl) -1-piperazinyl]propanol (510 mg; 2.0 mmol) in toluene (30 ml) and refluxed for 16 h. The solvent was evaporated rated and the residue resuspended in ethyl acetate, filtered and evaporated to dryness. The residue was submitted to flash chromatography on silica gel 60 eluting with toluene/ethyl acetate (1:1) graduated to toluene/ethyl acetate (1:3). The product was taken up in ethanol, which was treated with hydrogen chloride in ether to give 730 mg of the title compound. M.p. 211°-212° C. MS (70 eV): m/z 477 (4%, M+), 254 (56), 221 (59), 209 (100), 158 (35), 138 (25), 111 (20), 70 (45).

Workup

  1. temperaturewas refluxed for 6 h
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b58f39396da84e4494e3cd059717395f
Source dataset
uspto-grants-1993_09
Patent number
US05246935

Reaction notes

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