Sodium Thiosulfate → HCID 89876061, compound

HRID 2169767Notes

Reaction equation

HRID 2169767 reaction equation
[Cl:1][C:2]1[N:3]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[N:15]=[C:16]([S:20][CH3:21])[C:17]=2[O:18][CH3:19])[C:4]2[C:9]([C:10]=1[Cl:11])=[CH:8][CH:7]=[CH:6][CH:5]=2.C1C=C(Cl)C=C(C(OO)=[O:32])C=1.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[N:3]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[N:15]=[C:16]([S:20]([CH3:21])=[O:32])[C:17]=2[O:18][CH3:19])[C:4]2[C:9]([C:10]=1[Cl:11])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 89876118HCID 89876118, compound

Product 1

HCID 89876061HCID 89876061, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-(2,3-dichloroindol-1-yl)-5-methoxy-2-methyl-6-methylsulfanyl-pyridazin-3-one (60 mg, 0.16 mmol) in DCM (2 mL) at −20° C. is added mCPBA (36 mg, 0.17 mmol). After stirring for 10 min at this temperature, a yellow precipitate had appeared. The reaction was poured into a mixture of DCM (20 mL), sodium bicarbonate saturated solution (10 mL) and sodium thiosulphate saturated solution (10 mL), then stirred for 10 min. The resulting mixture was then passed through a phase separator and the DCM layer was concentrated under reduced pressure to afford the desired product 4-(2,3-dichloroindol-1-yl)-5-methoxy-2-methyl-6-methylsulflnyl-pyridazin-3-one (59 mg, 0.12 mmol, 95%) as a yellow solid, which was used without further purification.

Workup

  1. stirringstirred for 10 min
  2. concentrationthe DCM layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-72d605345b144500bd24e91ef2dbf60a
Source dataset
uspto-grants-2015_06
Patent number
US09049864B2

Reaction notes

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