3-Chloro-6-hydroxyacetophenone → N-[(E)-1-(5-chloro-2-hydroxyphenyl)ethylideneamino]-3-(dimethylsulfamoyl)benzamide

HRID 877612Notes

Reaction equation

[NH:1]([C:3]([C:5]1[CH:6]=[C:7]([S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1)=[O:4])[NH2:2].[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([OH:27])=[C:22]([C:24](=O)[CH3:25])[CH:23]=1>CO.C(O)(=O)C>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([OH:27])=[C:22](/[C:24](=[N:2]/[NH:1][C:3]([C:5]2[CH:6]=[C:7]([S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=2)=[O:4])/[CH3:25])[CH:23]=1

Participants

Conditions

Temperature: 120 °C

Procedure

3-(Hydrazinecarbonyl)-N,N-dimethylbenzenesulfonamide (50 mg, 0.206 mmol) and 1-(5-chloro-2-hydroxyphenyl)ethanone (35.1 mg, 0.206 mmol) were dissolved in methanol (4 mL) in the presence of acetic acid as a catalyst, and the reaction mixture was heated via microwave irradiation to 120° C. for 30 min. The reaction was monitored by TLC. Upon completion of the reaction and following cooling, the solvent was removed by vacuum, and the resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2) affording the title compound as a solid (15 mg). 1H NMR (400 MHz, acetone-d6): δ 8.29 (m, 2H), 8.01 (d, 1H, J=8.4 Hz), 7.83 (t, 1H, J=8.4 Hz), 7.62 (d, 1H, J=2.4 Hz), 7.32 (dd, 1H, J=2.4 & 8.8 Hz), 6.96 (d, 1H, J=8.8 Hz), 2.73 (s, 6H), 2.58 (s, 3H). ESI-MS: 396.0 [M+H]+.

Workup

customUpon completion of the reaction
temperaturefollowing cooling
customthe solvent was removed by vacuum
customthe resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2)

Sources & evidence

ORD record: ord-69eb91d72d1e49208588a579938fce99
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987335B2

Reaction notes

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