Chloroacetonitrile → 3-Amino-5-phenylselenophene-2-carbonitrile

HRID 2408953Notes

Reaction equation

Cl[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH:3][C:4]#[N:5].[Se-2:12].[Na+].[Na+].Cl[CH2:16][C:17]#[N:18]>>[NH2:5][C:4]1[CH:3]=[C:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[Se:12][C:16]=1[C:17]#[N:18]

Participants

Reactant 3

HCID 7856Chloroacetonitrile

HCID 73973Sodium selenide

HCID 27775113-Chloro-3-phenyl-2-propenenitrile

Product 1

HCID 866468883-Amino-5-phenylselenophene-2-carbonitrileYield 53%

Procedure

The reaction of 3-chloro-3-phenylprop-2-enenitrile, sodium selenide and chloroacetonitrile as described earlier gave the product as a brown color solid (4.8 g, 53%), mp 162-164° C. (decomp). 1H NMR (400 MHz, CDCl3): δ 7.46-7.49 (2H, m), 7.37-7.39 (3H, m), 7.01 (1H, s), 4.55 (2H, br s).

Sources & evidence

ORD record: ord-9478aa3fdc764589bb16a3f3187981d6
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815879B2

Reaction notes

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