m-Chloroperbenzoic acid → HCID 12791053, compound

HRID 1155243Notes

Reaction equation

HRID 1155243 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[CH2:5][N:6]([C:26]([S:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[CH2:7][P:8]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=1)([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=1)=[O:9])[CH3:2].ClC1C=CC=C(C(OO)=[O:45])C=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:36])[CH2:5][N:6]([C:26]([S:28]([CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:45])=[O:27])[CH2:7][P:8]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=1)([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=1)=[O:9])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12791037HCID 12791037, compound

Product 1

HCID 12791053HCID 12791053, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl-N-[(benzylthio)carbonyl]-N-[bis(3-methylphenoxy)phosphinylmethyl]-glycinate (2.6 g.; 0.005 mol.) dissolved in 25 ml. of methylene chloride at 0° C. was added metachloroperbenzoic acid (1.02 g.; 0.005 mol.). The reaction mixture was stirred at 0° C. for 5.25 hours, filtered and the filtrate was washed with 5% sodium hydroxide, dried, and concentrated in vacuo. To remove any remaining solvent, the residue was concentrated at 25° C. and 0.05 mm. and yielded ethyl-N-[(benzylsulfinyl)carbonyl]-N-[bis(3-methylphenoxy)phosphinylmethyl]-glycinate as an oil (nD25 =1.5584) having the following analysis:

Workup

  1. filtrationfiltered
  2. washthe filtrate was washed with 5% sodium hydroxide
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customTo remove any remaining solvent
  6. concentrationthe residue was concentrated at 25° C.

Sources & evidence

ORD record
ord-73bd819dff574d65a6fbf62680558317
Source dataset
uspto-grants-1981_11
Patent number
US04300942

Reaction notes

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