Ethanesulfonyl chloride → 4-Ethylsulphonyl-2,3,4,5-tetrahydro-1,4-benzothiazepine

HRID 1079338Notes

Reaction equation

HRID 1079338 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[S:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][NH:10][CH2:9][CH2:8]1>ClCCl>[CH2:1]([S:3]([N:10]1[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[S:7][CH2:8][CH2:9]1)(=[O:5])=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 122691062,3,4,5-Tetrahydrobenzo[f][1,4]thiazepine

Product 1

HCID 98815744-Ethylsulphonyl-2,3,4,5-tetrahydro-1,4-benzothiazepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethanesulphonyl chloride (3.8 g) in dichloromethane (50 ml) was added dropwise at room temperature to a stirred solution of 2,3,4,5-tetrahydro-1,4-benzothiazepine (4.29 g, prepared as described in the first paragraph of Example 6 above) in dichloromethane (100 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 trichloromethane as eluent gave 4-ethylsulphonyl-2,3,4,5-tetrahydro-1,4-benzothiazepine, which was recrystallised from hexane. Yield 4.25 g (m.p. 78°-80° C.).

Workup

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

Sources & evidence

ORD record
ord-1296b15049f148c2a3068159c381ea79
Source dataset
uspto-grants-1996_12
Patent number
US05580866

Reaction notes

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