Benzonitrile → HCID 178439043, compound

HRID 925013Notes

Reaction equation

[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].C([Li])CCC.[C:19](#[N:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[NH:6][C:19](=[NH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:13])[CH3:12]

Participants

Reactant 3

HCID 7505Benzonitrile

HCID 32484Diisopropylaniline

HCID 178418339Butyllithium

Product 1

HCID 178439043HCID 178439043, compoundYield 50%

Procedure

Procedure as described for Amidine I using the following amounts: 8.50 mL of 2,6-diisopropylaniline (45.0 mmol); 23.5 mL of 2.0 M butyllithium (47.0 mmol); 4.70 mL of benzonitrile (46.0 mmol). Filtration of the final pentane solution yielded 6.31 g (50%) of white solid. 1H NMR (400 MHz, CDCl3): 7.92 (d, 2H), 7.48 (m, 3H), 7.17 (d, 2H), 7.09 (t, 1 H), 4.59 (s, 2H), 3.06 (septet, 2H), 1.20 (d, 12H).

Workup

filtrationFiltration of the final pentane solution

Sources & evidence

ORD record: ord-7fc64d44f44e4664ab218d7ab7416191
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09283555B2

Reaction notes

Loading…