Phenol → HCID 54284133, compound

HRID 1448429Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:15][C:16]([F:34])([F:33])[C:17]([N:19]([CH2:26][P:27]([O:31]Cl)([O:29]Cl)=[O:28])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:18].[CH2:35]([SH:37])[CH3:36]>CCOCC>[F:15][C:16]([F:34])([F:33])[C:17]([N:19]([CH:26]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[P:27]([OH:31])([O:29][S:37][CH2:35][CH3:36])=[O:28])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of phenol (2.68 g, 0.0285 mole) and triethylamine (3.97 ml, 0.0285 mole) in 50 ml. of ether was added to a solution of ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (9.9 g, 0.03 mole) in 175 ml. of ether at 0° C. After three hours, the reaction mixture was filtered and the cooled (0° C.) filtrate was treated with a solution of ethanethiol (2.13 ml, 0.0285 mole) and triethylamine (3.97 ml, 0.0285 mole) in 50 ml. of ether. After stirring at 25° C. overnight, the solution was filtered and the filtrate was washed with 1.5% hydrochloric acid, 1.5% ammonium hydroxide and saturated sodium chloride solution. Concentration in vacuo afforded an oil which was chromatographed on silica gel eluting with ethyl acetate/cyclohexane (1:1) to yield ethyl N-trifluoroacetyl-N-(phenoxy(ethylthio)phosphonomethyl)glycinate (1.5 g) as a clear oil, ND25 =1.4969.

Workup

customat 0° C
filtrationthe reaction mixture was filtered
filtrationthe solution was filtered
washthe filtrate was washed with 1.5% hydrochloric acid, 1.5% ammonium hydroxide and saturated sodium chloride solution
concentrationConcentration in vacuo
customafforded an oil which
customwas chromatographed on silica gel eluting with ethyl acetate/cyclohexane (1:1)

Sources & evidence

ORD record: ord-072bc33d2d7246a888718d99d2b40ef0
Source dataset: uspto-grants-1979_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04180394

Reaction notes

Loading…