Water → 4-Nitrophenyl thiomorpholine-4-carboxylate 1-oxide

HRID 220030Notes

Reaction equation

HRID 220030 reaction equation
[N:1]1([C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[O:8])[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:27])C=1.O>ClCCl>[N:1]1([C:7]([O:9][C:10]2[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=2)=[O:8])[CH2:2][CH2:3][S:4](=[O:27])[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 581164954-Nitrophenyl thiomorpholine-4-carboxylate

Product 1

HCID 581165434-Nitrophenyl thiomorpholine-4-carboxylate 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

13.1 g (49.0 mmol) of 4-nitrophenyl thiomorpholine-4-carboxylate were initially charged in 135 ml of dichloromethane and admixed at 0° C. with 7.6 g (44.1 mmol) of m-chloroperbenzoic acid in portions. The mixture was stirred at RT for two hours, water was added and the organic phase was removed. The organic phase was washed rapidly with saturated aqueous sodium hydrogencarbonate solution, filtered and concentrated under reduced pressure. The crude product was purified by means of preparative HPLC. Yield: 7.8 g (56% of theory)

Workup

  1. customthe organic phase was removed
  2. washThe organic phase was washed rapidly with saturated aqueous sodium hydrogencarbonate solution
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-cb3e826cc9b44cc08b789c167fe2fcab
Source dataset
uspto-grants-2012_06
Patent number
US08202862B2

Reaction notes

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