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3-(Morpholine-4-sulfonyl)benzohydrazide → N-[(E)-1-(2-chloro-4-pyridinyl)ethylideneamino]-3-morpholin-4-ylsulfonylbenzamide

HRID 877603
Notes
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Reaction equation

HRID 877603 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=O)[CH3:9])[CH:5]=[CH:4][N:3]=1.[O:11]1[CH2:16][CH2:15][N:14]([S:17]([C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=2)[C:23]([NH:25][NH2:26])=[O:24])(=[O:19])=[O:18])[CH2:13][CH2:12]1>CO.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6](/[C:8](=[N:26]/[NH:25][C:23](=[O:24])[C:22]2[CH:27]=[CH:28][CH:29]=[C:20]([S:17]([N:14]3[CH2:15][CH2:16][O:11][CH2:12][CH2:13]3)(=[O:18])=[O:19])[CH:21]=2)/[CH3:9])[CH:5]=[CH:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 8772463-(Morpholine-4-sulfonyl)benzohydrazideHCID 131452551-(2-Chloropyridin-4-yl)ethan-1-one

Product 1

HCID 72792612N-[(E)-1-(2-chloro-4-pyridinyl)ethylideneamino]-3-morpholin-4-ylsulfonylbenzamideYield 60%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

1-(2-Chloropyridin-4-yl)ethanone (20 mg, 0.129 mmol) and 3-(morpholinosulfonyl)benzohydrazide (36.7 mg, 0.129 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. Following cooling, the solvent was removed by vacuum and the resulting crude material was purified by flash column chromatography affording the title compound in a 60% yield. 1H NMR (400 MHz, CDCl3): δ 9.43 (m, 1H), 8.39 (m, 2H), 8.15 (d, 1H, J=8.0 Hz), 7.93 (d, 1H, J=7.6 Hz), 7.70 (t, 1H, J=7.6 Hz), 7.52 (m, 1H), 3.73 (m, 4H), 3.02 (m, 4H), 2.35 (s, 3H). ESI-MS: 423.1 [M+H]+.

Workup

  1. temperatureFollowing cooling
  2. customthe solvent was removed by vacuum
  3. customthe resulting crude material was purified by flash column chromatography

Sources & evidence

ORD record
ord-93fcc9e9b4b848b4ad6b6ab7c7531697
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08987335B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes