Water → 4-Acryloyl-2-[4-methoxyphenyl]-7-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine
Reaction equation
[C:1]([N:5]1[CH2:11][C:10]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:9]=2[S:8][CH:7](Cl)[CH2:6]1)(=[O:4])[CH:2]=[CH2:3].[C:19]1([O:25][CH3:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C(Cl)Cl>[C:1]([N:5]1[CH2:11][C:10]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:9]=2[S:8][CH:7]([C:22]2[CH:23]=[CH:24][C:19]([O:25][CH3:26])=[CH:20][CH:21]=2)[CH2:6]1)(=[O:4])[CH:2]=[CH2:3]Participants
Procedure
The above-mentioned 4-acryloyl-2-chloro-7-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine (2.3 g) and anisole (1.1 g) were dissolved in methylene chloride (50 ml) and stannic chloride (2.8 g) was added thereto and agitated at room temperature for 2 hours. To the reaction mixture water was added and extracted with chloroform. The chloroform phase was washed with a saturated saline solution and dried on sodium sulfate and thereafter the solvent was distilled out under reduced pressure. Residue was purified by silica gel column chromatography (Wako Gel C-200, 50 g) and eluted with a mixed solvent of n-hexane (70 parts)+ethyl acetate (30 parts) to give 4-acryloyl-2-[4-methoxyphenyl]-7-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine (1.7 g).
Workup
- extractionextracted with chloroform
- washThe chloroform phase was washed with a saturated saline solution
- customdried on sodium sulfate
- distillationthe solvent was distilled out under reduced pressure
- customResidue was purified by silica gel column chromatography (Wako Gel C-200, 50 g)
- washeluted with a mixed solvent of n-hexane (70 parts)+ethyl acetate (30 parts)
Sources & evidence
- ORD record
- ord-4a411b1b7007494db70c36a9bc8ed7aa
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05416066
Reaction notes
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