Acrylonitrile → 4,9-Dithiadodecanedinitrile

Reaction equation

[CH2:1]([SH:6])[CH2:2][CH2:3][CH2:4][SH:5].[C:7](#[N:10])[CH:8]=[CH2:9].[OH-].[CH2:12]([N+:19](C)(C)C)[C:13]1C=CC=C[CH:14]=1>>[C:12](#[N:19])[CH2:13][CH2:14][S:5][CH2:4][CH2:3][CH2:2][CH2:1][S:6][CH2:9][CH2:8][C:7]#[N:10]

Participants

Reactant 3

HCID 7855Acrylonitrile

HCID 66854Benzyltrimethylammonium hydroxide

HCID 791481,4-Butanedithiol

Product 1

HCID 215072244,9-Dithiadodecanedinitrile

Procedure

4,9-Dithiadodecanedinitrile was prepared according to the procedure of Example 1 using 1,4-butanedithiol (20.0 g; 0.16 moles), acrylonitrile (17.0 g; 0.32 moles) and benzyltrimethylammonium hydroxide (40% in methanol; 1 ml) as the catalyst.

Sources & evidence

ORD record: ord-ebfc0ec332534ab8a406278d927751e3
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03984336

Reaction notes

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