Thiophosgene → 4-Methylsulfonylphenylisothiocyanate
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
Product 1
Reagents, catalysts & solvents 2
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
- filtrationthe suspension was filtered
- washwashed with water
- dry with materialdried over P2O5
Sources & evidence
- ORD record
- ord-e092182de60b48639366dedfe02287ff
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07423053B2
Reaction notes
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