Sodium hydride → 2-Methylthio-5-diethylphosphonomethylthio-1,3,4-thiadiazole

HRID 2297021Notes

Reaction equation

HRID 2297021 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]([SH:8])=[N:6][N:7]=1.[H-].[Na+].FC(F)(F)S(O[CH2:17][P:18]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19])(=O)=O>C1COCC1>[CH3:1][S:2][C:3]1[S:4][C:5]([S:8][CH2:17][P:18]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19])=[N:6][N:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11833487(Diethoxyphosphoryl)methyl trifluoromethanesulfonateHCID 1785036205-methylsulfanyl-1,3,4-thiadiazole-2-thiol

Product 1

HCID 537638322-Methylthio-5-diethylphosphonomethylthio-1,3,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-methylthio-1,3,4-thiadiazole-5-thiol (1 mmole) in THF (5 mL) was treated with sodium hydride (60%, 1.1 mmole) at 0° C. and the resulting mixture was stirred at room temperature for 30 min. The reaction was then cooled to 0° C. and treated with diethylphosphonomethyl trifluoromethanesulfonate (1.1 mmole). After stirring at room temperature for 12 h, the reaction was quenched with saturated ammonium chloride. Extraction and chromatography gave 2-methylthio-5-diethylphosphonomethylthio-1,3,4-thiadiazole as an oil.

Workup

  1. temperatureThe reaction was then cooled to 0° C.
  2. stirringAfter stirring at room temperature for 12 h
  3. customthe reaction was quenched with saturated ammonium chloride
  4. extractionExtraction and chromatography

Sources & evidence

ORD record
ord-5199d7b17a3f4c9598654061e124bd80
Source dataset
uspto-grants-2002_12
Patent number
US06489476B1

Reaction notes

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