Sodium Thiosulfate → HCID 19592642, compound

HRID 613518Notes

Reaction equation

HRID 613518 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2)=[O:5].ClC1C=CC=C(C(OO)=[O:30])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)CCl>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N+:15]([O-:30])=[CH:14][CH:13]=[CH:12]2)=[O:5]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 19592470HCID 19592470, compound

Product 1

HCID 19592642HCID 19592642, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 8-(2,6-dichlorobenzoylamino)quinoline (100 mg) and m-chloroperbenzoic acid (71 mg) in ethylene chloride was stirred for 1 hour at 40° C. To the mixture was added 5% sodium thiosulfate solution, and the mixture was partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from dichloromethane-methanol to give 8-(2,6-dichlorobenzoylamino)quinoline 1-oxide (48 mg).

Workup

  1. customthe mixture was partitioned between dichloromethane and saturated sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was recrystallized from dichloromethane-methanol

Sources & evidence

ORD record
ord-d383037a16884140a92cb835e62b0819
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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