Sodium Thiosulfate → HCID 59428142, compound

HRID 502842Notes

Reaction equation

HRID 502842 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-999ab500835d486487366979e09bc62a
Source dataset
uspto-grants-2010_08
Patent number
US07776877B2

Reaction notes

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