Aminoacetonitrile → HCID 46197437, compound

HRID 2360347Notes

Reaction equation

HRID 2360347 reaction equation
[CH2:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[NH2:18][CH2:19][C:20]#[N:21]>>[C:19]([CH2:20][NH:21][C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:17][CH:16]=1)#[N:18]

Participants

3

Reactant 2

HCID 10901AminoacetonitrileHCID 19147p-Octylbenzoic acid

Product 1

HCID 46197437HCID 46197437, compound

Procedure

General procedure F was used to couple 0.1 g (0.42 mmols) of 2 and 0.065 g of amino acetonitrile. The title product was purified with flash chromatography using a solvent system of ethyl acetate and hexanes (2:3) to yield 0.104 g (0.38 mmols). 1H NMR (300 MHz, CDCl3) δ 7.70 (d, J=8.3, 2H), 7.25 (d, J=7.6, 2H), 6.78 (t, J=5.5, 1H), 4.37 (d, J=5.8, 2H), 2.81-2.51 (m, 2H), 1.62 (dt, J=7.4, 22.1, 3H), 1.26 (s, 10H), 0.87 (t, J=6.7, 3H). 13C NMR (75 MHz, CDCl3) δ 167.32, 148.82, 130.03, 129.08, 127.46, 117.30, 77.67, 77.25, 76.83, 36.09, 32.06, 31.35, 29.62, 29.44, 28.19, 22.86, 14.31.

Workup

  1. customThe title product was purified with flash chromatography
  2. customto yield 0.104 g (0.38 mmols)

Sources & evidence

ORD record
ord-a4a7b74ff28242a9996ad679ef91647f
Source dataset
uspto-grants-2014_04
Patent number
US08686046B2

Reaction notes

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