Hydrochloric Acid → 4-Ethylsulphonyl-6-chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine

HRID 1079339Notes

Reaction equation

HRID 1079339 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[Cl:7][C:8]1[C:13]2[CH2:14][NH:15][CH2:16][CH2:17][S:18][C:12]=2[CH:11]=[CH:10][CH:9]=1.Cl.C(N(CC)CC)C>ClCCl>[CH2:1]([S:3]([N:15]1[CH2:14][C:13]2[C:8]([Cl:7])=[CH:9][CH:10]=[CH:11][C:12]=2[S:18][CH2:17][CH2:16]1)(=[O:5])=[O:4])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 101981056-Chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine

Product 1

HCID 233666774-Ethylsulphonyl-6-chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethanesulphonyl chloride (1.28 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 as eluent gave 4-ethylsulphonyl-6-chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine, which was recrystallised from ethyl acetate/hexane. Yield 2.53 g (m.p. 126°-128° 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-83413fc529ae43c3a14d0629d49d9166
Source dataset
uspto-grants-1996_12
Patent number
US05580866

Reaction notes

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