1-Aminocyclopropanecarbonitrile → HCID 68182923, compound

HRID 1484065Notes

Reaction equation

[NH2:1][C:2]1([C:5]#[N:6])[CH2:4][CH2:3]1.[C:7](Cl)(=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>>[C:5]([C:2]1([NH:1][C:7](=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:4][CH2:3]1)#[N:6]

Participants

Reactant 2

HCID 5568881-Aminocyclopropanecarbonitrile

HCID 5364783Oleoyl chloride

Product 1

HCID 68182923HCID 68182923, compoundYield 74%

Procedure

General procedure F was used to 1.68 mmols of 1-amino-1-cyclopropanecarbonitrile to 2.184 mmols of oleoyl chloride. After standard purification techniques, 1.24 mmols (74%) of the title product was recovered. 1H NMR (500 MHz, CDCl3) δ 6.53 (s, 1H), 5.43-5.25 (m, 2H), 2.17 (t, J=7.6, 2H), 1.99 (dd, J=6.5, 12.5, 4H), 1.60 (d, J=7.2, 2H), 1.52 (dd, J=5.7, 8.3, 2H), 1.39-1.15 (m, 24H), 0.87 (t, J=6.9, 3H). 13C NMR (126 MHz, CDCl3) δ 174.09, 130.00, 129.66, 120.14, 97.26, 35.97, 31.88, 29.74, 29.68, 29.51, 29.30, 29.23, 29.14, 29.09, 27.20, 27.14, 25.22, 22.66, 20.39, 16.74, 14.11.

Sources & evidence

ORD record: ord-5694025ccf8a4ea8909ec3a8bc40fa94
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09421177B2

Reaction notes

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