o-Iodonitrobenzene → HCID 24821367, compound

HRID 1931268Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[C:11]([NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>>[C:3]1([N:8]2[C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N:26]=[C:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1

Participants

Reactant 2

HCID 69115o-Iodonitrobenzene

HCID 69324Myristanilide

Product 1

HCID 24821367HCID 24821367, compoundYield 69%

Procedure

Method A applied to 1-iodo-2-nitrobenzene (125 mg, 0.5 mmol) and myristanilide (182 mg, 0.6 mmol) yielded the title compound as colorless oil (130 mg, 69%). 1H NMR (DMSO) δ 0.74 (t, J=6.9Hz, 3H), 1.14-1.28 (m, 20H), 1.68 (p, J=7.6Hz, 2H), 2.83 (t, J=7.6Hz, 2H), 7.14 (d, J=8.1Hz, 1H), 7.29 (dd, J=8.1, 7.7Hz, 1H), 7.47 (dd, J=8.1, 7.7Hz, 1H), 7.56-7.68 (m, 5H), 7.74 (d, J=7.7Hz, 1H); 13C NMR δ 13.9, 22.0, 26.3, 26.4, 28.3, 28.4, 28.7, 28.8, 28.9, 29.9, 31.2, 110.7, 116.9, 123.5, 123.7, 127.2, 129.6, 130.1, 134.2, 135.0, 137.6, 154.7. HRMS (FAB): cal. for C26H36N2 [M+H+]: 377.2957; found: 377.2953. Method C afforded 149 mg of the title compound (79% yield).

Sources & evidence

ORD record: ord-2b04413a819c49c5a2ea14dbf3c7877d
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188282B2

Reaction notes

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