Diethyl Ether → HCID 19828389, compound

HRID 1788701Notes

Reaction equation

HRID 1788701 reaction equation
[C:1]([C:3]1[C:4]([S:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[N:5][CH:6]=[C:7]([CH2:9][Br:10])[CH:8]=1)#[N:2].[CH2:21]([P:25]([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH3:24].CCOCC>O1CCCC1>[Br-:10].[C:1]([C:3]1[C:4]([S:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[N:5][CH:6]=[C:7]([CH2:9][P+:25]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:21][CH2:22][CH2:23][CH3:24])[CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 13831TributylphosphineHCID 139125515-(Bromomethyl)-2-[(4-nitrophenyl)sulfanyl]pyridine-3-carbonitrile

Product 1

HCID 19828389HCID 19828389, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Alternatively, 3-cyano-2-(4-nitrophenylthio)-5-bromomethylpyridine is allowed to react in tetrahydrofuran with tri-(n-butyl)phosphine for ten hours. Following the addition of ether, the solid which forms is collected by filtration and washed with 1:1 tetrahydrofuran:ether to yield [3-cyano-2-(4-nitrophenylthio)pyridin-5-ylmethyl]-tri-(n-butyl)phosphonium bromide as a white solid; mp 175°-176° C.; NMR (CDCl3, 80 MHz) d 0.85-2.63 (m, 27H), 4.76 (d, 2H, J=15.4 Hz), 7.74 (d, 2H, J=9.0 Hz), 8.26 (d, 2H, J=9.0 Hz), 8.55 (brs, 1H), 8.79 (brs, 1H); IR (KBr) 2950, 2860, 2220, 1595, 1575, 1515, 1390, 1340, 1075 and 845 cm-1 ; HRMS 471.2116 (M+ -HBr), Calc'd. for C25H34N3O2PS471.2109.

Workup

  1. filtrationthe solid which forms is collected by filtration
  2. washwashed with 1:1 tetrahydrofuran

Sources & evidence

ORD record
ord-30c38e6c44134c8aa3772aafb891d2a6
Source dataset
uspto-grants-1987_08
Patent number
US04684653

Reaction notes

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