Methanol → HCID 53930935, compound

HRID 1448419Notes

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.[Cl:30][C:31]1[CH:32]=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=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][O:37][C:33]1[CH:34]=[CH:35][CH:36]=[C:31]([Cl:30])[CH:32]=1)=[O:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (8.25 g, 0.025 mole) in 100 ml. of ether was cooled to 0° C. and treated with a solution of methanol (1.01 ml, 0.025 mole) and triethylamine (3.49 ml, 0.025 mole) in 100 ml. of ether. After two hours, the mixture was filtered and the filtrate was cooled to 0° C. and treated with a solution of m-chlorophenol (3.21 g, 0.025 mole) and triethylamine (3.49 ml, 0.025 mole) in 100 ml. of ether. The resulting solution was stirred overnight at 25° C., filtered and the filtrate concentrated in vacuo. The residue was extracted into petroleum ether and the resulting solution was concentrated in vacuo to yield ethyl N-trifluoroacetyl-N-(methoxy(m-chlorophenoxy)phosphonomethyl)glycinate as a yellow oil (7.55 g), ND =1.4803.

Workup

filtrationthe mixture was filtered
filtrationfiltered
concentrationthe filtrate concentrated in vacuo
extractionThe residue was extracted into petroleum ether
concentrationthe resulting solution was concentrated in vacuo

Sources & evidence

ORD record: ord-6d21b37aeab14985a6ad1ff0287eff0d
Source dataset: uspto-grants-1979_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04180394

Reaction notes

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