Methanethiol → HCID 53742705, compound

HRID 1448420Notes

Reaction equation

HRID 1448420 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([N:5]([CH2:10][P:11]([O:15]Cl)([O:13]Cl)=[O:12])[CH2:6][C:7]([O-:9])=[O:8])=[O:4].[CH3:19][OH:20].C(N([CH2:26][CH3:27])CC)C.[CH3:28][SH:29]>CCOCC>[F:1][C:2]([F:18])([F:17])[C:3]([N:5]([CH:10]([O:20][CH3:19])[P:11]([OH:15])([O:13][S:29][CH3:28])=[O:12])[CH2:6][C:7]([O:9][CH2:26][CH3:27])=[O:8])=[O:4]

Participants

6

Reactant 4

HCID 878MethanethiolHCID 887MethanolHCID 8471Triethylamine2×HCID 86736746HCID 86736746, compound

Product 1

HCID 53742705HCID 53742705, compoundYield 24.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (8.25 g, 0.025 mole) in 100 ml. of ether was cooled to 0° C. and a solution of methanol (1.01 ml, 0.025 mole) and triethylamine (3.49 ml, 0.025 mole) in 30 ml. of ether was added. After two hours, the reaction mixture was filtered and the filtrate was cooled to 0° C. and treated with methanethiol (1.38 ml, 0.025 mole) and triethylamine (3.49 ml, 0.025 mole). This mixture was stirred overnight, then concentrated in vacuo to afford an oil which was chromatographed on silica gel. The column was eluted with methylene chloride/ethyl acetate to yield ethyl N-trifluoroacetyl-N-(methoxy(methylthio)phosphonomethyl)glycinate (2.3 g) as an oil, ND =1.4571.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customto afford an oil which
  4. customwas chromatographed on silica gel
  5. washThe column was eluted with methylene chloride/ethyl acetate

Sources & evidence

ORD record
ord-c9ccd1d97ada470e939d9aa7ebacdd5c
Source dataset
uspto-grants-1979_12
Patent number
US04180394

Reaction notes

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