2-Mercaptoethanol → 3-{[2-(2-Cyanoethoxy)ethyl]sulfanyl}propanenitrile

Reaction equation

[SH:1][CH2:2][CH2:3][OH:4].[C:5](#[N:8])[CH:6]=[CH2:7].[OH-].[CH2:10]([N+:17](C)(C)C)[C:11]1C=CC=C[CH:12]=1>>[C:10](#[N:17])[CH2:11][CH2:12][O:4][CH2:3][CH2:2][S:1][CH2:7][CH2:6][C:5]#[N:8]

Participants

Reactant 3

HCID 15672-Mercaptoethanol

HCID 7855Acrylonitrile

HCID 66854Benzyltrimethylammonium hydroxide

Product 1

HCID 2200353-{[2-(2-Cyanoethoxy)ethyl]sulfanyl}propanenitrile

Procedure

4-Oxa-7-thiadecanedinitrile was prepared according to the procedure of Example 1 using 2-mercaptoethanol (25.0 g; 0.32 moles), acrylonitrile (34.0 g; 0.64 moles) and benzyltrimethylammonium hydroxide (40% in methanol; 1 ml) as the catalyst.

Sources & evidence

ORD record: ord-a8b355b3865f4037948200fd35e91e53
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03984336

Reaction notes

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