P-Toluenesulfonylhydrazide → 4-Cyano-2-(2-(3,4-dichlorophenyl)ethylsulfonamido)benzenesulfonamide

HRID 2283317Notes

Reaction equation

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

Participants

Conditions

Temperature: 180 °C

Procedure

(E)-4-Cyano-2-(2-(3,4-dichlorophenyl)vinylsulfonamido)benzenesulfonamide (123 mg, 0.28 mmol), sodium acetate (93 mg, 1.14 mmol) and para-toluenesulfonhydrazide (212 mg, 1.14 mmol) were dissolved in anhydrous tetrahydrofuran (3 mL) in a microwave vial. The vial was capped and evacuated two times with argon. The mixture was heated in a microwave at 180° C. for 15 min. The mixture was filtered and the solvent was evaporated in vacuo. Purification twice by preparative HPLC gave 4.8 mg (4% yield) of the title compound.

Workup

customThe vial was capped
customevacuated two times with argon
filtrationThe mixture was filtered
customthe solvent was evaporated in vacuo
customPurification twice by preparative HPLC

Sources & evidence

ORD record: ord-224f0dfa8fda4579bc3ee406a3a89493
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145380B2

Reaction notes

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