Hydrochloric Acid → 6-Chloro-4-methylsulphinyl-2,3,4,5-tetrahydro-1,4-benzothiazepine

HRID 1079331

Reaction equation

HRID 1079331 reaction equation
[CH3:1][S:2](Cl)=[O:3].[Cl:5][C:6]1[C:11]2[CH2:12][NH:13][CH2:14][CH2:15][S:16][C:10]=2[CH:9]=[CH:8][CH:7]=1.Cl.C(N(CC)CC)C>ClCCl>[Cl:5][C:6]1[C:11]2[CH2:12][N:13]([S:2]([CH3:1])=[O:3])[CH2:14][CH2:15][S:16][C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 548463Methanesulfinyl chlorideHCID 10198105HCID 10198105, compound

Product 1

HCID 98816666-Chloro-4-methylsulphinyl-2,3,4,5-tetrahydro-1,4-benzothiazepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulphinyl chloride (0.98 g) in dichloromethane (10 ml) was added dropwise at room temperature to a stirred solution of 6-chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine (1.99 g, prepared in a similar manner to its hydrochloride, Example 1 above) and triethylamine (1.01 g) in dichloromethane (50 ml). The reaction mixture was stirred at room temperature for one hour, washed with water, dried and the solvent was removed by evaporation. Purification of the residue by flash chromatography using dichloromethane/ethanol (98:2) as eluent gave 6-chloro-4-methylsulphinyl-2,3,4,5-tetrahydro-1,4-benzothiazepine, which was recrystallised from ethylacetate/hexane. Yield 2.1 g (m.p. 82°-84° C.).

Workup

  1. washwashed with water
  2. customdried
  3. customthe solvent was removed by evaporation
  4. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-a4b39ac55d1746fba3b43ffd23dfb566
Source dataset
uspto-grants-1996_12
Patent number
US05580866

Linked notes

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