P-Toluenesulfonylhydrazide → HCID 57751061, compound

HRID 2283370Notes

Reaction equation

HRID 2283370 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[C:4]([NH:12][S:13](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]([F:27])[F:26])=[CH:20][CH:19]=2)(=[O:15])=[O:14])[CH:3]=1.C([O-])(=O)C.[Na+].C1(C)C=CC(S(NN)(=O)=O)=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[C:4]([NH:12][S:13]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]([F:26])[F:27])=[CH:20][CH:19]=2)(=[O:14])=[O:15])[CH:3]=1

Participants

5

Reactant 3

HCID 15303P-ToluenesulfonylhydrazideHCID 517045Sodium AcetateHCID 57751055HCID 57751055, compound

Product 1

HCID 57751061HCID 57751061, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
180 °C

Procedure

(E)-4-Chloro-2-(2-(4-(difluoromethoxy)phenyl)vinylsulfonamido)benzenesulfonamide (0.426 g, 0.97 mmol) was dissolved in anhydrous tetrahydrofuran (2 mL). Sodium acetate (0.318 g, 3.88 mmol) and p-toluenesulfonic acid hydrazide (0.723 g, 3.88 mmol) were added and the reaction was heated in a microwave at 180° C. for 60 min. The mixture was filtered and the solvent was evaporated under vacuum. Purification by preparative HPLC, gave 41 mg (10% yield) of the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated under vacuum
  3. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-a5847221917b4b84ad529bca78b2f13e
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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