Water → 4-Acryloyl-2-chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine

HRID 36566Notes

Reaction equation

[C:1]([N:5]1[CH2:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[S:8][CH2:7][CH2:6]1)(=[O:4])[CH:2]=[CH2:3].S(Cl)([Cl:19])(=O)=O.O>C(Cl)Cl>[C:1]([N:5]1[CH2:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[S:8][CH:7]([Cl:19])[CH2:6]1)(=[O:4])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 0 °C

Procedure

4-Acryloyl-2,3,4,5-tetrahydro-1,4-benzothiazepine (10 g) was dissolved in methylene chloride (150 ml) and sulfuryl chloride (9.3 g) was added thereto under ice cooling and agitated at 0° C. for 1 hour. 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, 200 g) and eluted with a mixed solvent of n-hexane (70 parts)+ethyl acetate (30 parts) to give 4-acryloyl-2-chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine (10.5 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, 200 g)
washeluted with a mixed solvent of n-hexane (70 parts)+ethyl acetate (30 parts)

Sources & evidence

ORD record: ord-b2097bd393d941eab59637fdf0eff87a
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05416066

Reaction notes

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