Ethanethiol → HCID 54198579, compound
Reaction equation
[CH2:1]([SH:3])[CH3:2].[CH2:4](N(CC)CC)[CH3:5].C([CH:13]([C:28]([OH:30])=[O:29])[N:14]([C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[CH2:15][P:16]([O:20]Cl)([O:18]Cl)=[O:17])C.[CH:31]([NH2:34])([CH3:33])[CH3:32]>CCOCC>[F:26][C:23]([F:24])([F:25])[C:22]([N:14]([CH:15]([NH:34][CH:31]([CH3:33])[CH3:32])[P:16]([OH:18])([O:20][S:3][CH2:1][CH3:2])=[O:17])[CH2:13][C:28]([O:30][CH2:4][CH3:5])=[O:29])=[O:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of ethanethiol (2.13 ml, 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)glycine (9.9 g, 0.03 mole) in 150 ml. of ether at 0° C. The resulting mixture was stirred for three hours, then filtered and the cooled (0° C.) filtrate was treated with a solution of isopropylamine (4.85 ml, 0.057 mole) in 50 ml. of ether. After stirring overnight, the reaction mixture was filtered and washed with 1.5% hydrochloric acid, 1.5% ammonium hydroxide and saturated aqueous sodium chloride. The resulting solution was concentrated in vacuo to afford an oil which was recrystallized from ethyl acetate-cyclohexane (1:5) to give ethyl N-trifluoroacetyl-N-(isopropylamino(ethylthio)phosphonomethyl)glycinate as a white solid, m.p. 85°-87° C.
Workup
- customat 0° C
- filtrationfiltered
- stirringAfter stirring overnight
- filtrationthe reaction mixture was filtered
- washwashed with 1.5% hydrochloric acid, 1.5% ammonium hydroxide and saturated aqueous sodium chloride
- concentrationThe resulting solution was concentrated in vacuo
- customto afford an oil which
- customwas recrystallized from ethyl acetate-cyclohexane (1:5)
Sources & evidence
- ORD record
- ord-9a21f20f519744d89f4da3fb196e5fd2
- Source dataset
- uspto-grants-1979_12
- Patent number
- US04180394
Reaction notes
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