3-(Trifluoromethyl)aniline → 1-Isothiocyanato-3-(trifluoromethyl)benzene

HRID 1851676Notes

Reaction equation

HRID 1851676 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[C:12](Cl)(Cl)=[S:13].C(OCC)(=O)C>C(Cl)Cl.CCCCCC>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([N:6]=[C:12]=[S:13])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 8857Ethyl AcetateHCID 10040Thiophosgene

Product 1

HCID 1372321-Isothiocyanato-3-(trifluoromethyl)benzeneYield 76.19%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

To a stirred solution of 3-(trifluoromethyl)aniline (20 g, 124.2 mmol) in DCM (100 mL) was added thiophosgene (21.24 g, 186.4 mmol) at 5-10° C. and the reaction mixture was stirred at room temperature for 1-2 h. The reaction was monitored by TLC (mobile phase-40% ethyl acetate in n-Hexane, Rf. S.M.—0.25, product—0.5). Upon disappearance of the starting material, the reaction mass was diluted with DCM, the organic layer was washed with 10% NaHCO3, water and brine. The organic layer was dried and concentrated in vacuo at a temperature lower than 45° C. to afford the product as a yellow oil (Yield: 19.2 g, 76.19% of theoretical).

Workup

  1. washthe organic layer was washed with 10% NaHCO3, water and brine
  2. customThe organic layer was dried
  3. concentrationconcentrated in vacuo at a temperature lower than 45° C.

Sources & evidence

ORD record
ord-637d8c80133046698ab985e7e9d3ec56
Source dataset
uspto-grants-2015_02
Patent number
US08957216B2

Reaction notes

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