2-Tosylbenzaldehyde → 2-(3-methoxyphenyl)-N-[(E)-[2-(p-tolylsulfonyl)phenyl]methyleneamino]acetamide

HRID 1795116Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[CH:13]=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH2:27][C:28]([NH:30][NH2:31])=[O:29])[CH:24]=[CH:25][CH:26]=1>CCO>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH2:27][C:28]([NH:30]/[N:31]=[CH:13]/[C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[O:29])[CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-[(4-methylphenyl)sulfonyl]benzaldehyde (500 mg, 1.92 mmol) in EtOH (10 mL) is added 2-(3-methoxyphenyl)acetohydrazide (329 mg, 1.92 mmol) and the reaction is heated to 80° C. for 1 h. While cooling a white precipitate forms, and this solid is isolated by filtration and washed with portions of EtOH and Et2O. This solid was dried under vacuum to provide 2-(3-methoxyphenyl)-N′-((1E)-{2-[(4-methylphenyl)sulfonyl]phenyl}methylene)acetohydrazide (313 mg, 39%). 1H-NMR (400 MHz, DMSO-d6) 12.00–11.85 (m, 1H), 8.95–8.80 (m, 1H), 8.16–8.10 (m, 1H), 7.99–7.81 (2H), 7.72–7.65 (m, 2H), 7.42–7.37 (m, 2H), 7.27–7.16 (m, 1H), 6.93–6.76 (m, 4H), 3.92–3.36 (m, 5H), 2.35 (s, 3H). ESI+ for C23H22N2O4S, m/z: 423, (M+H)+.

Workup

temperatureWhile cooling a white precipitate forms
customthis solid is isolated by filtration
washwashed with portions of EtOH and Et2O
customThis solid was dried under vacuum

Sources & evidence

ORD record: ord-c932edc8c1d349488b991d3e093dd0a0
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026339B2

Reaction notes

Loading…