Sodium methanethiolate → HCID 14155314, compound

HRID 649467Notes

Reaction equation

HRID 649467 reaction equation
[CH3:1][S-:2].[Na+].FC(F)(F)CO[C:8]1[CH:13]=[CH:12][N:11]2[N:14]=[C:15]([S:17]([NH:20][C:21]3[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:28])(=[O:19])=[O:18])[N:16]=[C:10]2[N:9]=1>CS(C)=O.Cl>[CH3:1][S:2][C:8]1[CH:13]=[CH:12][N:11]2[N:14]=[C:15]([S:17]([NH:20][C:21]3[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:28])(=[O:19])=[O:18])[N:16]=[C:10]2[N:9]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 14155312HCID 14155312, compound

Product 1

HCID 14155314HCID 14155314, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

To 25 ml (13 mmol) of a 0.52M solution of sodium methyl mercaptide in DMSO prepared by bubbling methyl mercaptan into a suspension of sodium hydride in DMSO, was added 2.6 g (5.9 mmol) of 5-(2,2,2-trifluoroethoxy)-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide. The solution was stirred at room temperature for 25 hours, diluted with 100 ml of ice water and neutralized with 3N aqueous HCl. The gummy solid which separated was collected and taken up in 0.5N aqueous NaOH. The mixture was filtered to remove insoluble material, and the fitrate was acidified with 6N aqueous HCl. The solid which separated was collected by filtration and dried to yield 1.5 g (66%) of the desired product as a pale yellow solid, mp 239°-243° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. customby bubbling methyl mercaptan
  2. additioninto a suspension of sodium hydride in DMSO
  3. customThe gummy solid which separated
  4. customwas collected
  5. filtrationThe mixture was filtered
  6. customto remove insoluble material
  7. customThe solid which separated
  8. filtrationwas collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-8eefe18786154ccd915ba2518e11432d
Source dataset
uspto-grants-1988_04
Patent number
US04740233

Reaction notes

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