m-Chloroperbenzoic acid → HCID 15230147, compound

HRID 1721576Notes

Reaction equation

HRID 1721576 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]1([S:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][CH:24]([P:33](=[O:40])([O:37][CH2:38][CH3:39])[O:34][CH2:35][CH3:36])[P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[C:12]1([S:18]([CH2:19][CH2:20][CH2:21][CH2:22][NH:23][CH:24]([P:33](=[O:40])([O:37][CH2:38][CH3:39])[O:34][CH2:35][CH3:36])[P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])=[O:9])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 9934281HCID 9934281, compound

Product 1

HCID 15230147HCID 15230147, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

m-Chloroperbenzoic acid (487 rag) was added in small portions to a solution of tetraethyl 4-(phenylthio)butylaminomethylenebisphosphonate (1.20 g) in dichloromethane (10 ml) with ice-cooling, and then the mixture was stirred at 0° C. for 2 hours. The reaction mixture was washed successively with aqueous sodium bisulfite, saturated aqueous sodium bicarbonate, and water and then dried (MgSO4), and concentrated. The residue was chromatographed on silica gel. Tetraethyl 4-(phenylsulfinyl)butylaminomethylenebisphosphonate was obtained as a colorless oil (1.05 g, 85%) from the fraction eluted with chloroformmethanol (50:1, v/v).

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed successively with aqueous sodium bisulfite, saturated aqueous sodium bicarbonate, and water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-2e53f273b495414dba11d9d0a6c0f7a6
Source dataset
uspto-grants-1996_04
Patent number
US05512552

Reaction notes

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