Dimethylformamide → 2-Chloro-6-fluorophenylisothiocyanate

HRID 514240Notes

Reaction equation

HRID 514240 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH2:9].[C:10](Cl)(Cl)=[S:11].CN(C=O)C>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]=[C:10]=[S:11]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10040ThiophosgeneHCID 27342052-Chloro-6-fluoroaniline

Product 1

HCID 265991402-Chloro-6-fluorophenylisothiocyanateYield 96.4%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a solution of 2-chloro-6-fluorobenzenamine (5.0 g, 34 mmol) in chlorobenzene (52 mL) was added carbonothioic dichloride (thiophosgene) (5.1 g, 45 mmol) and DMF (0.27 mL). The reaction mixture was refluxed for 2 h and then concentrated to leave the title compound as a brown oil (6.15 g), which was used in Step C without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9befb20dcda74fe7a217375152cf105d
Source dataset
uspto-grants-2015_08
Patent number
US09107412B2

Reaction notes

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