Acrylonitrile → Propanenitrile, 3-(2-benzothiazolylthio)-

HRID 1287202Notes

Reaction equation

HRID 1287202 reaction equation
[SH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[OH-].[CH2:12]([N+:19](C)(C)C)[C:13]1C=CC=C[CH:14]=1.C(#N)C=C>C(O)(C)(C)C>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[S:1][CH2:14][CH2:13][C:12]#[N:19]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 178418395HCID 178418395, compound

Product 1

HCID 1796554Propanenitrile, 3-(2-benzothiazolylthio)-

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

2-Mercaptobenzothiazole (25.0 g; 0.15 moles) was mixed with t-butanol (125 ml) and benzyltrimethylammonium hydroxide (40% in methanol; 3 ml). Acrylonitrile (15.9 g; 0.30 moles) was added dropwise and the mixture stirred at room temperature for 7 days. The product was removed by filtration and recrystallized from benzene.

Workup

  1. customThe product was removed by filtration
  2. customrecrystallized from benzene

Sources & evidence

ORD record
ord-28cb5a382b9f446e8c29876a8c517677
Source dataset
uspto-grants-1976_10
Patent number
US03984336

Reaction notes

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