m-Chloroperbenzoic acid → 6-Chloro-4-methylsulphonyl-2,3,4,5-tetrahydro-1,4-benzothiazepine 1-oxide

HRID 1079335Notes

Reaction equation

HRID 1079335 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[C:18]2[CH2:19][N:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH2:21][CH2:22][S:23][C:17]=2[CH:16]=[CH:15][CH:14]=1>ClCCl>[Cl:12][C:13]1[C:18]2[CH2:19][N:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH2:21][CH2:22][S:23](=[O:9])[C:17]=2[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 233666796-Chloro-4-methylsulphonyl-2,3,4,5-tetrahydro-1,4-benzothiazepine

Product 1

HCID 233666876-Chloro-4-methylsulphonyl-2,3,4,5-tetrahydro-1,4-benzothiazepine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-chloroperbenzoic acid (2.26 g) in dichloromethane (150 ml) was added dropwise with cooling from 0° C. to -2° C. to a stirred solution of 6-chloro-4-methylsulphonyl-2,3,4,5-tetrahydro-1,4-benzothiazepine (3.05 g, prepared as Example 19 above) in dichloromethane (100 ml). The reaction mixture was stirred for 15 minutes, washed with water and dried, and the solvent was removed by evaporation at reduced pressure. Purification of the residue by flash chromatography using dichloromethane/ethanol (95:5) as eluent gave 6-chloro-4-methylsulphonyl-2,3,4,5-tetrahydro-1,4-benzothiazepine 1-oxide, which was recrystallised from ethyl acetate. Yield 2.86 g (m.p. 167°-169° C.).

Workup

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

Sources & evidence

ORD record
ord-cd755516cb0f4766ae16648f7dbf74e3
Source dataset
uspto-grants-1996_12
Patent number
US05580866

Reaction notes

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