4-Dodecylbenzoic acid → N-(1-cyanocyclopropyl)-4-dodecylbenzamide
Reaction equation
[CH2:1]([C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl.[NH2:23][C:24]1([C:27]#[N:28])[CH2:26][CH2:25]1>>[C:27]([C:24]1([NH:23][C:17](=[O:19])[C:16]2[CH:15]=[CH:14][C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:21][CH:20]=2)[CH2:26][CH2:25]1)#[N:28]Participants
3
Procedure
General procedure G was used to convert 4-dodecylbenzoic acid (0.52 mmols) to the corresponding acyl chloride. After standard work up procedures, the intermediate was immediately subjected to conditions described in general procedure F in the presence of 1-amino-1-cyclopropanecarbonitrile hydrochloride (0.4 mmols). After flash chromatography, 0.15 mmols of the title product was recovered. 1H NMR (500 MHz, CDCl3) δ 7.68 (d, J=7.1, 2H), 7.23 (d, J=7.5, 2H), 6.82 (s, 1H), 2.63 (t, J=7.7, 2H), 1.65-1.57 (m, 4H), 1.35 (t, J=7.0, 2H), 1.29-1.25 (m, 17H), 0.88 (t, J=6.5, 3H). 13C NMR (126 MHz, CDCl3) δ 167.81, 148.06, 130.01, 128.75, 127.19, 120.07, 35.85, 31.89, 31.11, 29.61, 29.53, 29.42, 29.32, 29.20, 22.66, 20.88, 16.97, 14.08.
Sources & evidence
- ORD record
- ord-543d0a6044fd4dec8fc0d6ff3b285324
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09421177B2
Reaction notes
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