Acrylonitrile → 1-[2-(2-Cyanoethoxy)ethyl]-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazole

HRID 2291332Notes

Reaction equation

HRID 2291332 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[OH:5][CH2:6][CH2:7][N:8]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:21])=[N:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[N:9]1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>C(#N)C>[C:1]([CH2:2][CH2:3][O:5][CH2:6][CH2:7][N:8]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:21])=[N:15][CH2:16][C:17]([F:19])([F:18])[F:20])=[N:9]1)#[N:4]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 212798481-(2-Hydroxyethyl)-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazole

Product 1

HCID 212798521-[2-(2-Cyanoethoxy)ethyl]-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazoleYield 32.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Acrylonitrile (0.8 g.) was added to a solution of 1-(2-hydroxyethyl)-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazole (2.51 g.) in acetonitrile (10 ml.). Benzyltrimethylammonium hydroxide (40% w/v aqueous solution; 10 μl) was added. After stirring at room temperature for 1 hour, the solution was evaporated to dryness in vacuo, and the residue purified by medium pressure chromatography using triethylamine/EtOH/EtOAc 1:1:9 v/v/v as eluant to give 1-[2-(2-cyanoethoxy)ethyl]-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazole (1.0 g.) having the following n.m.r. spectrum in d6DMSO: 7.6 (d, 1H); 5.8 (d, 1H); 4.2 (m, 2H); 4.1 (t, 2H); 3.8 (t, 2H); 3.6 (t, 2H); 2.7 (t, 2H).

Workup

  1. customthe solution was evaporated to dryness in vacuo
  2. customthe residue purified by medium pressure chromatography

Sources & evidence

ORD record
ord-7b8d7cd5fbd64af0bc7a87c651418e01
Source dataset
uspto-grants-1989_01
Patent number
US04795755

Reaction notes

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