m-Chloroperbenzoic acid → 4-Acetyl-2,3,4,5-tetrahydro-1,4-benzothiazepine 1-oxide

HRID 1079323Notes

Reaction equation

HRID 1079323 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([N:15]1[CH2:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[S:18][CH2:17][CH2:16]1)(=[O:14])[CH3:13]>ClCCl>[C:12]([N:15]1[CH2:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[S:18](=[O:9])[CH2:17][CH2:16]1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 146707161-(2,3-Dihydro-1,4-benzothiazepin-4(5H)-yl)ethanone

Product 1

HCID 233666804-Acetyl-2,3,4,5-tetrahydro-1,4-benzothiazepine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-chloroperbenzoic acid (1.03 g) in dichloromethane (100 ml) was added dropwise with cooling from 0° C. to -2° C. to a stirred solution of 4-acetyl-2,3,4,5-tetrahydro-1,4-benzothiazepine (1.03 g, prepared as Example 7 above) in dichloromethane (50 ml). The reaction mixture was stirred for 15 minutes, then washed with water, dried and the solvent was removed by evaporation at reduced pressure. Purification of the residue by flash chromatography using dichloromethane/ethanol (9:1) as eluent gave 4-acetyl-2,3,4,5-tetrahydro-1,4-benzothiazepine 1-oxide, which was recrystallised from ethyl acetate. Yield 0.67 g (m.p. 156°-157° 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-ac0ad43324354903b155ff0fc8ba8018
Source dataset
uspto-grants-1996_12
Patent number
US05580866

Reaction notes

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