Phenol → HCID 54547547, compound

HRID 1448422Notes

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].[C:21]1([OH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C.[C:35]1([SH:41])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CCOCC>[F:1][C:2]([F:20])([F:19])[C:3]([N:5]([CH:12]([O:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[P:13]([OH:17])([O:15][S:41][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=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 ether (150 ml.) was cooled to 0° C. and a solution of phenol (2.35 g, 0.025 mole) and triethylamine (3.49 ml, 0.025 mole) in 50 ml. of ether was added to it. The resulting mixture was stirred for three hours, then filtered. The filtrate was cooled to 0° C. and thiophenol (2.5 ml, 0.025 mole) and triethylamine (3.49 ml, 0.025 mole) in 50 ml. of ether was added. The resulting solution was stirred overnight at 25° C., filtered and concentrated in vacuo. The residue was chromatographed on silica eluting first with methylene chloride, then with ether to yield ethyl N-trifluoroacetyl-N-(phenoxy(phenylthio)phosphonomethyl)glycinate (7.97 g) as a white solid, m.p. 80°-82° C.

Workup

filtrationfiltered
stirringThe resulting solution was stirred overnight at 25° C.
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica eluting first with methylene chloride

Sources & evidence

ORD record: ord-809e0b2b99c14bf9a71bf1eabf858ca9
Source dataset: uspto-grants-1979_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04180394

Reaction notes

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