Palmitoyl chloride → HCID 68182879, compound

HRID 1484064Notes

Reaction equation

[NH2:1][C:2]1([C:5]#[N:6])[CH2:4][CH2:3]1.[C:7](Cl)(=[O:23])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>>[C:5]([C:2]1([NH:1][C:7](=[O:23])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:4][CH2:3]1)#[N:6]

Participants

Reactant 2

HCID 8206Palmitoyl chloride

HCID 5568881-Aminocyclopropanecarbonitrile

Product 1

HCID 68182879HCID 68182879, compoundYield 77.4%

Procedure

General procedure F was used to couple 1.68 mmols of 1-amino-1-cyclopropanecarbonitrile to 2.184 mmols of palmitoyl chloride. After standard purification techniques, 1.3 mmols (77%) of the title product was recovered. 1H NMR (500 MHz, CDCl3) δ 5.95 (s, 1H), 2.16 (t, J=7.6, 2H), 1.65-1.59 (m, 2H), 1.58 (s, 1H), 1.57-1.53 (m, 2H), 1.39-1.15 (m, 28H), 0.88 (dd, J=6.0, 7.0, 3H). 13C NMR (126 MHz, CDCl3) δ 119.97, 36.08, 31.91, 29.64, 25.17, 22.68, 20.32, 16.85, 14.25.

Sources & evidence

ORD record: ord-e8839f33fbe14b1fba2f968344470821
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09421177B2

Reaction notes

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