Sodium methanethiolate → HCID 23288278, compound

HRID 368294Notes

Reaction equation

HRID 368294 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]2[CH:13]=[C:12]([CH2:14][CH3:15])[O:11][N:10]=2)=[CH:4][N:3]=1.[CH3:16][S-:17].[Na+]>C(O)(C)(C)C>[Cl:8][C:7]1[C:2]([S:17][CH3:16])=[N:3][CH:4]=[C:5]([C:9]2[CH:13]=[C:12]([CH2:14][CH3:15])[O:11][N:10]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 23288263HCID 23288263, compound

Product 1

HCID 23288278HCID 23288278, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

3-(2,3-Dichloro-5-pyridyl)-5-ethylisoxazole (0.71 g, 2.9 mmol) was dissolved in t-butanol (15 mL) and sodium methanethiolate (0.3 g, 4.3 mmol) added. The reaction mixture was heated under reflux with stirring for 3 hours, cooled, and poured onto ice. The resulting cream precipitate was collected by filtration, dissolved in dichloromethane (50 mL) and dried over anhydrous sodium sulphate. Evaporation of the solvent under reduced pressure gave the desired product (0.61 g, 83%) as a cream solid, melting point. 59-62° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux
  3. temperaturecooled
  4. additionpoured onto ice
  5. filtrationThe resulting cream precipitate was collected by filtration
  6. dissolutiondissolved in dichloromethane (50 mL)
  7. dry with materialdried over anhydrous sodium sulphate
  8. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-5671cecd452b409dbcbc1072fe42c1ca
Source dataset
uspto-grants-2000_10
Patent number
US06133294

Reaction notes

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