Sodium Thiosulfate → HCID 178493773, compound

HRID 845516Notes

Reaction equation

HRID 845516 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][N:6]=[C:5]([CH2:11][S:12][C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:21][C:15]=3[N:14]=2)[CH:4]=1.Cl[O-].[Na+].S([O-])([O-])(=[O:33])=S.[Na+].[Na+]>O1CCOCC1.[OH-].[Na+]>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][N:6]=[C:5]([CH2:11][S:12]([C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:21][C:15]=3[N:14]=2)=[O:33])[CH:4]=1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 23665760Sodium HypochloriteHCID 178493767HCID 178493767, compound

Product 1

HCID 178493773HCID 178493773, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

0.8 g of 2-[(4,5-dimethoxy-2-pyridyl)methylthio]-5-(2,2,2-trifluoroethoxy)-1H-benzimidazole is dissolved in 15 ml of dioxane and 2.5 ml of 1N sodium hydroxide solution. A mixture of 3 ml of 8% strength sodium hypochlorite solution and 3.5 ml of 1N sodium hydroxide solution are added dropwise in the course of 2 hours, while cooling to 0°-5° C. After addition of 5 ml of 5% strength sodium thiosulfate solution, the mixture is concentrated to dryness, the residue is taken up in water and the mixture is brought to pH 7 with phosphate buffer. The solid which has precipitated out is filtered off with suction, dried and recrystallized from ethyl acetate/diisopropyl ether. 0.45 g (55% of theory) of the title compound is obtained as colorless crystals of m.p. 142°-143° C. (decomp.).

Workup

  1. additionare added dropwise in the course of 2 hours
  2. temperaturewhile cooling to 0°-5° C
  3. concentrationthe mixture is concentrated to dryness
  4. customThe solid which has precipitated out
  5. filtrationis filtered off with suction
  6. customdried
  7. customrecrystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-e6b3026bfe074d7c8efc35c53af78772
Source dataset
uspto-grants-1988_07
Patent number
US04758579

Reaction notes

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