M-Cresol → HCID 12791037, compound

HRID 1155238Notes

Reaction equation

C(N([CH2:6][CH3:7])CC)C.[CH2:8]([O:10][C:11](=[O:29])[CH2:12][N:13]([C:19]([S:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[CH2:14][P:15](Cl)(Cl)=[O:16])[CH3:9].[CH:30]1[C:35]([OH:36])=[CH:34][CH:33]=[CH:32][C:31]=1[CH3:37]>C(OCC)C>[CH2:8]([O:10][C:11](=[O:29])[CH2:12][N:13]([C:19]([S:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[CH2:14][P:15]([O:36][C:35]1[CH:34]=[CH:33][CH:32]=[C:6]([CH3:7])[CH:30]=1)([O:36][C:35]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:37])[CH:30]=1)=[O:16])[CH3:9]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of triethylamine (7.25 g.; 0.072 mol.) in 100 ml. of diethyl ether was added dropwise to a solution of freshly prepared ethyl-N-[(benzylthio)carbonyl]-N-[dichlorophosphinylmethyl]-glycinate (13.8 g.; 0.036 mol.) and m-cresol (7.8 g.; 0.072 mol.) dissolved in 150 ml. of diethyl ether. The reaction mixture was stirred for 16 hours at 25° C., then filtered. The filtrate was washed with 5% sodium hydroxide, 10% hydrochloric acid, and brine. The ether layer was separated, dried over magnesium sulfate and concentrated in vacuo. The residue was taken up in methylene chloride and again washed, dried and concentrated to yield ethyl-N-[(benzylthio)carbonyl]-N-[bis-(3-methylphenoxy)phosphinylmethyl]-glycinate as an oil (nD25 =1.5589) having the following analysis:

Workup

dissolutiondissolved in 150 ml
filtrationfiltered
washThe filtrate was washed with 5% sodium hydroxide, 10% hydrochloric acid, and brine
customThe ether layer was separated
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
washagain washed
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-76df2b7e9ed5440694b1cd226fbe65c3
Source dataset: uspto-grants-1981_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04300942

Reaction notes

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