Isatin → HCID 178444721, compound

HRID 1876253Notes

Reaction equation

[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[S:12]1[C:16]([C:17]([NH:19][NH2:20])=[O:18])=[CH:15][C:14]2[CH:21]=[CH:22][CH:23]=[CH:24][C:13]1=2>>[CH2:2]([N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)/[C:4](=[N:20]/[NH:19][C:17]([C:16]2[S:12][C:13]3[CH:24]=[CH:23][CH:22]=[CH:21][C:14]=3[CH:15]=2)=[O:18])/[C:2]1=[O:3])[CH2:4][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

Reactant 2

HCID 7054Isatin

HCID 519437benzo[b]thiophene-2-carbohydrazide

Product 1

HCID 178444721HCID 178444721, compoundYield 82%

Procedure

The title compound was prepared as a yellow solid, using isatin 3 and Benzo[b]thiophene-2-carboxylic hydrazide according to the synthetic method E. The resulting solid was washed with ethanol. Yield: 82%. 1H NMR (DMSO-d6): δ 0.86 (t, J=6.9 Hz, 3H), 1.26-1.36 (m, 6H), 1.64-1.66 (m, 2H), 3.79 (t, J=7.2 Hz, 2H), 7.19-7.27 (m, 2H), 7.48-7.59 (m, 3H), 7.75 (d, J=7.5 Hz, 1H), 8.13 (d, J=7.5 Hz, 2H), 8.31 (br s, 1H), 13.65 (br s, 1H). 13C NMR (DMSO-d6): δ 14.33 (CH3), 22.44 (CH2), 26.40 (CH2), 27.41 (CH2), 31.34 (CH2), 39.81 (CH2), 110.71 (CH), 115.52 (C), 119.55 (C), 121.52 (CH), 123.35 (CH), 123.69 (CH), 125.75 (CH), 126.51 (CH), 127.83 (CH), 132.38 (CH), 143.64 (C═N), 161.60 (C═O). HRMS (ES+) calcd for C23H24N3O2S(M+H+), m/e, 406.1596; found, 406.1584.

Workup

washThe resulting solid was washed with ethanol

Sources & evidence

ORD record: ord-8baa41064c204c7ca41f75ac055049d6
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309595B2

Reaction notes

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