Dimethylformamide →
Reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[S:15]2)[S:10][C:9]1=[S:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]1([CH3:36])[CH:30]=[CH:29][C:28]([S:31]([O:34]C)(=[O:33])=[O:32])=[CH:27][CH:26]=1.[CH3:37]N(C=O)C>CC(C)=O>[C:25]1([CH3:36])[CH:26]=[CH:27][C:28]([S:31]([O-:34])(=[O:32])=[O:33])=[CH:29][CH:30]=1.[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[S:15]2)[S:10][CH2+:9]1[S:24][CH3:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 3
Product 0
No Product data yet.
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
To a 200 mL flask was added 3-benzyl-5-(3-methylbenzothiazolin-2-ylidene)-2-thioxothiazolidin-4-one (5.00 g, 13.5 mmol), methyl p-toluenesulfonate (7.34 mL, 48.6 mmol) and anhydrous DMF(40 mL). After heating at 120° C. for 3 h, the mixture was allowed to cool to 60° C., transferred to a 1 L flask and diluted with acetone (400 mL). After cooling to room temperature, the precipitate was filtered under reduced pressure, washed first with acetone (50 mL) and then Et2O (100 mL), and dried under vacuum for 12 h to give the title product (6.25 g, 83%) as a yellow crystalline solid, which was used without further purification. 1H-NMR (CDCl3): δ 7.83 (1H, d), 7.75 (2H, m), 7.59–7.66 (2H, m), 7.50 (1H, m), 7.37–7.43 (5H, m), 7.06 (2H, d), 5.31 2H, s), 4.52 (3H, s), 3.22 (3H, s), 2.28 (3H, s).
Workup
- temperatureto cool to 60° C.
- customtransferred to a 1 L flask
- temperatureAfter cooling to room temperature
- filtrationthe precipitate was filtered under reduced pressure
- washwashed first with acetone (50 mL)
- dry with materialEt2O (100 mL), and dried under vacuum for 12 h
Sources & evidence
- ORD record
- ord-134831c59df140ab823e26333a7cd55b
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115640B2
Reaction notes
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