Triethylamine → 2,3,4-Trifluorophenyl isothiocyanate

HRID 1382739Notes

Reaction equation

HRID 1382739 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11](=S)[S-:12].C([NH+](CC)CC)C.C(N(CC)CC)C.C(Cl)(=O)OCC>C(Cl)(Cl)Cl>[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[N:10]=[C:11]=[S:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 16413959N,N-diethyl-1-ethanaminium N-(2,3,4-trifluorophenyl)carbamodithioate

Product 1

HCID 27607912,3,4-Trifluorophenyl isothiocyanateYield 78.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylammonium N-(2,3,4-trifluorophenyl)dithiocarbamate (92.0 g) and triethylamine (31.5 g) were added to chloroform (360 ml) and thereto ethyl chlorocarbonate (33.8 g) was added dropwise at 2°-6° C. with stirring over a period of 1 hour. The mixture was stirred for 10 minutes and washed with 3N hydrochloric acid and then with water. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica-gel column chromatography (Silica gel 60, 230-400 mesh, made by Merck Co., 220 g, eluent: hexane) under medium pressure, followed by distillation under reduced pressure to give the title compound (42.0 g) as colorless liquid, b.p.: 96°-97° C./17 mmHg.

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. washwashed with 3N hydrochloric acid
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica-gel column chromatography (Silica gel 60, 230-400 mesh, made by Merck Co., 220 g, eluent: hexane) under medium pressure
  6. distillationfollowed by distillation under reduced pressure

Sources & evidence

ORD record
ord-fb954e5e34894d5193e689d39daf86c3
Source dataset
uspto-grants-1989_02
Patent number
US04808584

Reaction notes

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