Methanethiol → HCID 22768209, compound

HRID 1973172Notes

Reaction equation

HRID 1973172 reaction equation
[CH3:1][SH:2].[OH-].[Na+].Cl[C:6]1[CH:7]=[CH:8][C:9]([N+:16]([O-:18])=[O:17])=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1>C(O)C>[N+:16]([C:9]1[CH:8]=[CH:7][C:6]([S:2][CH3:1])=[CH:11][C:10]=1[C:12]([F:15])([F:14])[F:13])([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 878MethanethiolHCID 14798Sodium HydroxideHCID 670525-Chloro-2-nitrobenzotrifluoride

Product 1

HCID 22768209HCID 22768209, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The sodium salt of methanethiol is formed by stirring a solution of methanethiol (100 g, 2.0 mole plus a slight excess), sodium hydroxide (80 g, 2.0 mole) and ethanol (2 l.) under nitrogen at 0°-5° C. for 1 hour. To this solution is rapidly added 5-chloro-2-nitrobenzotrifluoride (451.2 g, 2.0 mole). The solution is allowed to warm to room temperature overnight and then refluxed four hours, cooled, filtered and the solvent evaporated off under reduced pressure. The resulting oil is poured into cold water (1 l.), extracted with methylene chloride, dried over magnesium sulfate and the solvent evaporated under reduced pressure to afford a yellow solid. Recrystallization from hexane affords a product having a melting point of 47°-50° C.

Workup

  1. temperaturerefluxed four hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customthe solvent evaporated off under reduced pressure
  5. additionThe resulting oil is poured into cold water (1 l.)
  6. extractionextracted with methylene chloride
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent evaporated under reduced pressure
  9. customto afford a yellow solid
  10. customRecrystallization from hexane
  11. customaffords a product

Sources & evidence

ORD record
ord-febcfe2a95be420ab76242d297ff30b9
Source dataset
uspto-grants-1976_12
Patent number
US03996277

Reaction notes

Loading…