Benzoylhydrazine → HCID 178443230, compound

HRID 1876258Notes

Reaction equation

HRID 1876258 reaction equation
[CH2:1]([N:13]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:16](=O)[C:14]1=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:24]([NH:32][NH2:33])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:1]([N:13]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)/[C:16](=[N:33]/[NH:32][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)/[C:14]1=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

3

Reactant 2

HCID 11955BenzoylhydrazineHCID 1897797HCID 1897797, compound

Product 1

HCID 178443230HCID 178443230, compoundYield 100%

Procedure

The title compound was prepared as a pale orange solid, using 1-dodecyl-isatin and benzhydrazide according to the synthetic method D. The resulting solid was washed with ethanol. Yield: 100%. 1H NMR (DMSO-d6): δ 0.82 (t, J=6.6 Hz, 3H), 1.20-1.28 (m, 18H), 1.62-1.66 (m, 2H), 3.77 (t, J=6.9 Hz, 2H), 7.16-7.24 (m, 2H),7.48 (t, J=7.5 Hz, 1H), 7.60-7.73 (m, 4H), 7.92 (d, J=7.8 Hz, 2H), 13.91 (br s, 1H). 13C NMR (DMSO-d6): δ 14.38 (CH3), 22.53 (CH2), 26.67 (CH2), 27.38 (CH2), 29.07 (CH2), 29.14 (CH2), 29.32 (CH2), 39.36 (CH2), 29.43 (CH2), 29.45 (CH2), 31.73 (CH2), 39.75 (CH2), 110.68 (CH), 119.65 (C), 121.27 (CH), 123.70 (CH), 127.88 (CH), 129.65 (CH), 132.22 (CH), 132.41 (C), 133.40 (CH), 143.44 (C═N), 161.61 (C═O). HRMS (ES+) calcd for C27H36N3O2 (M+H+), m/e, 434.2812; found, 434.2802.

Workup

  1. washThe resulting solid was washed with ethanol

Sources & evidence

ORD record
ord-001c609a954c4012912a0dc36d015f75
Source dataset
uspto-grants-2012_11
Patent number
US08309595B2

Reaction notes

Loading…