Thiophosgene → 4-Methylsulfonylphenylisothiocyanate

HRID 30161

Reaction equation

HRID 30161 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:12](Cl)(Cl)=[S:13]>O.Cl>[N:11]([C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=1)=[C:12]=[S:13]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 796174-(Methylsulfonyl)aniline

Product 1

HCID 150782064-MethylsulfonylphenylisothiocyanateYield 85.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 4-methanesulfonylphenylamine (2.4 g, 14 mmol) was dissolved in a mixture of water (30 mL) and hydrochloric acid (9 mL, 37%). This was treated drop wise at room temperature with thiophosgene (1.5 g, 13.2 mmol) with good stirring. After 1 h, the suspension was filtered, washed with water and dried over P2O5 to give 2.4 g (85% yield) of 1-isothiocyanato4-methanesulfonylbenzene. 1H NMR (CDCl3), 300 MHz δ3.09 (s, 3H, CH3), 7.41(d, 2H, Aromatic), 7.98 (d, 2H, Aromatic).

Workup

  1. filtrationthe suspension was filtered
  2. washwashed with water
  3. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-e092182de60b48639366dedfe02287ff
Source dataset
uspto-grants-2008_09
Patent number
US07423053B2

Linked notes

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