Methanol → HCID 54452073, compound

HRID 1448418Notes

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]([N:5]([CH2:12][P:13]([O:17]Cl)([O:15]Cl)=[O:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:4].[CH3:21][OH:22].C(N(CC)CC)C.[C:30]1([SH:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CCOCC>[F:1][C:2]([F:20])([F:19])[C:3]([N:5]([CH:12]([O:22][CH3:21])[P:13]([OH:17])([O:15][S:36][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (6.6 g, 0.02 mole) was dissolved in 100 ml. of ether, cooled to 0° C. and treated with a solution of methanol (0.8 g, 0.02 mole) and triethylamine (2.78 g, 0.02 mole) in 50 ml. of ether. After two hours, the solution was filtered and the filtrate cooled to 0° C. and treated with a solution of thiophenol (2.05 ml, 0.02 mole) and triethylamine (2.78 ml, 0.02 mole) in 50 ml. of ether. After two hours, the solution was filtered and the filtrate was concentrated in vacuo. The residue was extracted into petroleum ether and the petroleum ether was removed by distillation in vacuo. The residue (1.5 g) was chromatographed on silica gel eluting with ether/benzene (7/3) to afford ethyl N-trifluoroacetyl-N-(methoxy(phenylthio)phosphonomethyl)glycinate as a colorless oil (1 g), ND =1.5047.

Workup

filtrationthe solution was filtered
waitAfter two hours
filtrationthe solution was filtered
concentrationthe filtrate was concentrated in vacuo
extractionThe residue was extracted into petroleum ether
customthe petroleum ether was removed by distillation in vacuo
customThe residue (1.5 g) was chromatographed on silica gel eluting with ether/benzene (7/3)

Sources & evidence

ORD record: ord-fd588240191c4dfa8da6214f25551936
Source dataset: uspto-grants-1979_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04180394

Reaction notes

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