P-Toluenesulfonylhydrazide → 5-Chloro-2-(2-(4-chloro-2-methoxyphenyl)ethylsulfonamido)benzenesulfonamide

HRID 2283334Notes

Reaction equation

C([O-])(=O)C.[Na+].C1(C)C=CC(S(NN)(=O)=O)=CC=1.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([NH:29][S:30](/[CH:33]=[CH:34]/[C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:36]=2[O:42][CH3:43])(=[O:32])=[O:31])=[C:23]([S:25]([NH2:28])(=[O:27])=[O:26])[CH:24]=1>O1CCCC1>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([NH:29][S:30]([CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:36]=2[O:42][CH3:43])(=[O:32])=[O:31])=[C:23]([S:25]([NH2:28])(=[O:26])=[O:27])[CH:24]=1

Participants

Conditions

Temperature: 180 °C

Procedure

Sodium acetate (64 mg, 0.78 mmol) and para-toluenesulfonhydrazide (145 mg, 0.78 mmol) was added to a solution of (E)-5-chloro-2-(2-(4-chloro-2-methoxyphenyl)vinylsulfonamido)benzenesulfonamide (85 mg, 0.19 mmol) in tetrahydrofuran (3 mL). The reaction mixture was heated at 180° C. for 15 min in a microwave reactor. The solids were removed by filtration, washed with tetrahydrofuran and the combined filtrates were evaporated. Purification by preparative HPLC gave 0.037 g (43% yield) of the title compound.

Workup

customThe solids were removed by filtration
washwashed with tetrahydrofuran
customthe combined filtrates were evaporated
customPurification by preparative HPLC

Sources & evidence

ORD record: ord-fc816705ef4d4e9db6e79c8753557056
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145380B2

Reaction notes

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