3-Thiocresol → n-decyl N-trifluoroacetyl-N-(bis(m-methylphenylthio)phosphonomethyl)glycinate

HRID 47011

Reaction equation

[F:1][C:2]([F:28])([F:27])[C:3]([N:5]([CH2:20][P:21]([O:25]Cl)([O:23]Cl)=[O:22])[CH2:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:8])=[O:4].[CH3:29][C:30]1[CH:31]=[C:32]([SH:36])[CH:33]=[CH:34][CH:35]=1.C(N([CH2:42][CH3:43])CC)C>CCOCC>[F:1][C:2]([F:28])([F:27])[C:3]([N:5]([CH2:20][P:21]([O:25][S:36][C:32]1[CH:31]=[CH:30][CH:29]=[C:42]([CH3:43])[CH:33]=1)([O:23][S:36][C:32]1[CH:33]=[CH:34][CH:35]=[C:30]([CH3:29])[CH:31]=1)=[O:22])[CH2:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:8])=[O:4]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of n-decyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (4.42 g, 0.01 mole) in 200 ml. of ether was added a solution of m-methylthiophenol (2.48 g, 0.02 mole) and triethylamine (2.02 g, 0.02 mole) in 50 ml. of ether. The resulting mixture was stirred for 16 hours at 20° C., then filtered. The filtrate was concentrated in vacuo to yield an oil which was chromatographed on silica gel (eluted with methylene chloride) to yield n-decyl N-trifluoroacetyl-N-(bis(m-methylphenylthio)phosphonomethyl)glycinate as an oil, nD27 =1.5267.

Workup

filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customto yield an oil which
customwas chromatographed on silica gel (eluted with methylene chloride)

Sources & evidence

ORD record: ord-a03f3ac4e3d3480db19e1447db288fff
Source dataset: uspto-grants-1979_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04175946

Linked notes

Loading…