m-Chloroperbenzoic acid → 4-(4-Nitrophenylmethyl)-thiomorpholine-1-oxide

HRID 24917Notes

Reaction equation

HRID 24917 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]2[CH2:27][CH2:26][S:25][CH2:24][CH2:23]2)=[CH:17][CH:16]=1)([O-:14])=[O:13]>ClCCl>[N+:12]([C:15]1[CH:16]=[CH:17][C:18]([CH2:21][N:22]2[CH2:27][CH2:26][S:25](=[O:9])[CH2:24][CH2:23]2)=[CH:19][CH:20]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 762900HCID 762900, compound

Product 1

HCID 225694274-(4-Nitrophenylmethyl)-thiomorpholine-1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11.7 g (58 mmol) of m-chloroperbenzoic acid are added to a solution of 11.5 g (48 mmol) of 4-(4-nitrophenylmethyl)-thiomorpholine in 100 ml of dichloromethane at ambient temperature. The reaction solution is stirred for 4 hours at ambient temperature and then washed with 1N sodium hydroxide solution and water and evaporated to dryness. Chromatography on silica gel (dichloromethane/methanol=9:1) yields the product.

Workup

  1. washwashed with 1N sodium hydroxide solution and water
  2. customevaporated to dryness
  3. customChromatography on silica gel (dichloromethane/methanol=9:1) yields the product

Sources & evidence

ORD record
ord-9ce3f739f6f342e7a5841edf4bd5d9e3
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

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