Hydrochloric Acid → 2-Chloro-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-4-phenylpyridine-3,5-dicarbonitrile

HRID 1630705Notes

Reaction equation

N[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([C:16]#[N:17])=[C:4]([S:18][CH2:19][C:20]2[N:21]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[S:23][CH:24]=2)[N:3]=1.N(OCCC(C)C)=O.[ClH:40]>C(#N)C.[Cu](Cl)Cl>[Cl:40][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([C:16]#[N:17])=[C:4]([S:18][CH2:19][C:20]2[N:21]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[S:23][CH:24]=2)[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

9 g (19.762 mmol) of 2-amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-4-phenylpyridine-3,5-dicarbonitrile are initially charged in 200 ml of acetonitrile, 7.98 ml (59.285 mmol) of isoamyl nitrite and 7.97 g (59.285 mmol) of copper(II) chloride are added and the mixture is stirred at 60° C. for 4 hours. 1N Hydrochloric acid is added to the mixture, and the precipitated solid is filtered off. It is purified on a silica gel column (mobile phase: toluene). This gives 5.98 g (63% of theory) of the target compound.

Workup

filtrationthe precipitated solid is filtered off
customIt is purified on a silica gel column (mobile phase: toluene)

Sources & evidence

ORD record: ord-2016e620c9484b61b960971a121710c7
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791146B2

Reaction notes

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