Sodium methanethiolate → HCID 12882536, compound

HRID 1492386Notes

Reaction equation

HRID 1492386 reaction equation
F[C:2]1[CH:11]=[C:10]([S:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:14][S-:15].[Na+]>CN(C)C=O>[CH3:14][S:15][C:2]1[CH:11]=[C:10]([S:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 18950257Methyl 2-fluoro-4-(methylthio)benzoate

Product 1

HCID 12882536HCID 12882536, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 2-fluoro-4-methylsulphenylbenzoate (4.1 g), sodium thiomethoxide (1.48 g) and N,N-dimethylformamide (16 ml) was stirred at 50° C. for 18 hours, poured onto water and extracted (ethyl acetate). The extract was washed (water), dried (magnesium sulphate) and evaporated to give methyl 2-methylsulphenyl-4-methylsulphenylbenzoate (2.09 g) as an orange oil, NMR (CDCl3) 2.0 (s,3H), 2.4 (s,3H), 3.65 (s,2H), 3.9 (s,3H), 7.05 (dd,1H), 7.15 (d,1H), 7.9 (d,1H).

Workup

  1. additionpoured onto water
  2. extractionextracted (ethyl acetate)
  3. washThe extract was washed (water)
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated

Sources & evidence

ORD record
ord-917cc09ac33a4fe0bfeb802fc6b94611
Source dataset
uspto-grants-1994_12
Patent number
US05374606

Reaction notes

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