Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]#[N:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:14](=O)([O-])[O-].[K+].[K+].[CH2:20]1[O:28][C:27]2[CH:26]=[CH:25][C:24]([N:29]=[C:30]=[S:31])=[CH:23][C:22]=2[O:21]1.CI.Cl>CC(C)=O>[O:28]1[C:27]2[CH:26]=[CH:25][C:24]([NH:29][C:30]([S:31][CH3:14])=[C:11]([S:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)(=[O:9])=[O:10])[C:12]#[N:13])=[CH:23][C:22]=2[O:21][CH2:20]1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-chlorophenylsulfonylacetonitrile (1.00 g, 4.64 mmol) in dry acetone (10 ml) first dry potassium carbonate (1.28 g, 9.3 mmol) and then 3,4-methylenedioxyphenyl isothiocyanate (0.87 g, 4.9 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 4 h, and then filtered. To the filtrate methyl iodide (0.86 ml, 13.9 mmol) was added. The mixture was stirred at room temperature for 50 min. Then pH was adjusted to 1 with 1N aqueous HCl. The precipitate was filtered off and washed with water to give 1.12 g (59%) of the title compound. Mp 196-200° C. 1H NMR (200 MHz, CDCl3): δ=2.22 (s, 3H), 6.05 (s, 2H), 6.68 (m, 2H), 6.80 (d, 1H), 7.53 (d, 2H), 7.87 (d, 2H), 9.80 (br s, 1H); EI SP/MS: 408 (M+).
Workup
- filtrationfiltered
- stirringThe mixture was stirred at room temperature for 50 min
- filtrationThe precipitate was filtered off
- washwashed with water
Sources & evidence
- ORD record
- ord-df307d1a16b44ba68b7776b2bb16215f
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06365609B1
Linked notes
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