Sodium Thiosulfate → HCID 59428142, compound

HRID 76020Notes

Reaction equation

HRID 76020 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[N:22]2[CH:26]=[C:25]([CH2:27][OH:28])[CH:24]=[N:23]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[N:22]2[CH:26]=[C:25]([CH:27]=[O:28])[CH:24]=[N:23]2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 59428115HCID 59428115, compound

Product 1

HCID 59428142HCID 59428142, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-tert-butyl-N-[4-chloro-2-(4-hydroxymethyl-pyrazol-1-yl)-phenyl]-benzenesulfonamide (synthesized according to general procedure LL, 31 mg, 0.074 mmol) in CH2Cl2 (3 mL) was added Dess-Martin periodinane (34 mg, 0.33 mmol) and the reaction was stirred for 3 hours at room temperature. 10% Na2S2O3 (5 mL) and saturated aqueous NaHCO3 (5 mL) were added sequentially and the mixture was stirred an additional 30 minutes. The aqueous layer was subsequently separated and extracted with EtOAc (2×25 mL). The combined organic layers were washed with saturated aqueous NaHCO3 solution (20 mL) and brine (20 mL), dried (anhydrous Na2SO4), and concentrated in vacuo to afford 4-tert-butyl-N-[4-chloro-2-(4-formyl-pyrazol-1-yl)-phenyl]-benzenesulfonamide which was used for further transformation without purification.

Workup

  1. stirringthe mixture was stirred an additional 30 minutes
  2. customThe aqueous layer was subsequently separated
  3. extractionextracted with EtOAc (2×25 mL)
  4. washThe combined organic layers were washed with saturated aqueous NaHCO3 solution (20 mL) and brine (20 mL)
  5. dry with materialdried (anhydrous Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b64e566b9f0843c387d41bb6d6c07ff0
Source dataset
uspto-grants-2014_09
Patent number
US08835468B2

Reaction notes

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