m-Chloroperbenzoic acid → HCID 12791031, compound

HRID 1413693Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:34])[CH2:5][N:6]([C:24]([S:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[CH2:7][P:8]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9])[CH3:2].ClC1C=CC=C(C(OO)=[O:43])C=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:34])[CH2:5][N:6]([C:24]([S:26]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:43])=[O:25])[CH2:7][P:8]([O:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([O:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:9])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of ethyl-N-[(benzylthio)carbonyl]-N-[bis(phenoxy)phosphinylmethyl]-glycinate (1.0 g.; 0.002 mol.) dissolved in 10 ml. of methylene chloride at 0° C. was slowly added a solution of metachloroperbenzoic acid (0.4 g.; 0.002 mol.) dissolved in 100 ml. of methylene chloride. The reaction mixture was stirred for one hour and allowed to gradually warm to 25° C. The mixture was washed with 5% sodium hydroxide, dried, then concentrated in vacuo. The resulting oil was extracted into hot petroleum ether and allowed to crystallize for 16 hours to yield ethyl-N-[(benzylsulfinyl)carbonyl]-N-[bis-(phenoxy) phosphinylmethyl]-glycinate as a solid having a melting point of 106°-115° C. and the following analysis:

Workup

dissolutiondissolved in 100 ml
washThe mixture was washed with 5% sodium hydroxide
customdried
concentrationconcentrated in vacuo
extractionThe resulting oil was extracted into hot petroleum ether
customto crystallize for 16 hours

Sources & evidence

ORD record: ord-4b05f041f18f42ee9bdcbc587abc844e
Source dataset: uspto-grants-1981_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04251258

Reaction notes

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