m-Chloroperbenzoic acid → Tetraethyl 6-(phenylsulfinyl)hexylaminomethylenebisphosphonate

HRID 54911Notes

Reaction equation

HRID 54911 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]1([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][CH:26]([P:35](=[O:42])([O:39][CH2:40][CH3:41])[O:36][CH2:37][CH3:38])[P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])[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][CH2:23][CH2:24][NH:25][CH:26]([P:35](=[O:42])([O:39][CH2:40][CH3:41])[O:36][CH2:37][CH3:38])[P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])=[O:9])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15227687HCID 15227687, compound

Product 1

HCID 54291626Tetraethyl 6-(phenylsulfinyl)hexylaminomethylenebisphosphonateYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (2.62 g) in limited amounts was added to a solution of tetraethyl 6-(phenylthio)hexylaminomethylenebisphosphonate (6.85 g) in dichloromethane (100 ml) under ice-cooling over 30 minutes. The reaction mixture was stirred under ice-cooling for 3 hours, and then washed with a saturated aqueous solution of sodium bicarbonate and water and dried (MgSO4). The solvent was distilled off under reduced pressure. The residual oil was subjected to column chromatography on silica gel. Tetraethyl 6-(phenylsulfinyl)hexylaminomethylenebisphosphonate (5.84 g, 82.6%) was obtained as an oil from the fractions obtained by elution with ethyl acetate-chloroform-methanol (10:10:1, v/v).

Workup

  1. temperaturecooling over 30 minutes
  2. temperaturecooling for 3 hours
  3. washwashed with a saturated aqueous solution of sodium bicarbonate and water
  4. dry with materialdried (MgSO4)
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-77416594a757494d9f2558fa6dafca83
Source dataset
uspto-grants-1997_04
Patent number
US05624917

Reaction notes

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