O,O-Dipyridin-2-yl carbonothioate → 2-Chloro-6-fluorophenylisothiocyanate

HRID 1406491Notes

Reaction equation

HRID 1406491 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH2:9].N1C=CC=CC=1O[C:17](=[S:25])OC1C=CC=CN=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]=[C:17]=[S:25]

Participants

4

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 27342052-Chloro-6-fluoroaniline

Product 1

HCID 265991402-Chloro-6-fluorophenylisothiocyanate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-chloro-6-fluoro-phenylamine (400 mg, 2.8 mmol), thiocarbonic acid O,O-dipyridin-2-yl ester (650 mg, 2.8 mmol) and TEA (840 μL, 6.0 mmol) in 5 mL THF was stirred overnight at 50° C. The mixture was heated to 65° C. and stirred for further 5 h. The mixture was concentrated i.vac. The residue was purified by chromatography on HPLC (C-18 Symmetry, eluent gradient: water+0.15% HCOOH+15-100% acetonitrile).

Workup

  1. temperatureThe mixture was heated to 65° C.
  2. stirringstirred for further 5 h
  3. concentrationThe mixture was concentrated i.vac
  4. customThe residue was purified by chromatography on HPLC (C-18 Symmetry, eluent gradient: water+0.15% HCOOH+15-100% acetonitrile)

Sources & evidence

ORD record
ord-a10ede9a4cbf4a10af44c3e5e95d71da
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

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