Sodium Thiosulfate → HCID 59718913, compound

HRID 1852531Notes

Reaction equation

HRID 1852531 reaction equation
CS[C:3]1[N:8]=[C:7]([N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[N:10]2)[CH:6]=[CH:5][N:4]=1.[CH:18]1C=C(Cl)C=C(C(OO)=O)C=1.[S:29]([O-:33])([O-])(=[O:31])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:18][S:29]([C:3]1[N:8]=[C:7]([N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[N:10]2)[CH:6]=[CH:5][N:4]=1)(=[O:33])=[O:31]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 59718927HCID 59718927, compound

Product 1

HCID 59718913HCID 59718913, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-(2-Methylsulfanyl-pyrimidin-4-yl)-1H-benzotriazole (27.05 g, 111 mmol) was dissolved/suspended in 600 mL of CHCl3 in a 2 L round bottom flask. The mixture was cooled with an ice bath and m-CPBA (58.03 g, 259 mmol, ca. 77%) was slowly added portionwise, while maintaining the reaction temperature below 15° C. The reaction mixture was slowly warmed to RT and stirred for 16 hours, then refluxed for 1 hour. It was cooled and treated with aqueous sodium thiosulfate; the organic layer was separated and washed with 3 portions of aqueous sodium bicarbonate. It was then dried over sodium sulfate, filtered and concentrated under reduced pressure until the formation of a suspension, which was filtered and dried to give the 1-(2-methanesulfonyl-pyrimidin-4-yl)-1H-benzotriazole as a white solid (20.78 g, 68% yield), mp=201.8-202.5° C.; MS=276 (M+H)+.

Workup

  1. temperatureThe mixture was cooled with an ice bath
  2. temperaturewhile maintaining the reaction temperature below 15° C
  3. temperaturerefluxed for 1 hour
  4. temperatureIt was cooled
  5. customthe organic layer was separated
  6. washwashed with 3 portions of aqueous sodium bicarbonate
  7. dry with materialIt was then dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure until the formation of a suspension, which
  10. filtrationwas filtered
  11. customdried

Sources & evidence

ORD record
ord-4290f1a55c3a4a39ac848e6e1502093e
Source dataset
uspto-grants-2015_02
Patent number
US08962622B2

Reaction notes

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