Diethyl Ether → HCID 18377673, compound

HRID 231290Notes

Reaction equation

HRID 231290 reaction equation
C(C1C(SC2C=CC([N+]([O-])=O)=CC=2)=NC=C(C[Br:10])C=1)#N.[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].[CH2:30]([PH+:25]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:26][CH2:27][CH2:28][CH3:29])[CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

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

Product 1

HCID 18377673HCID 18377673, 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 8 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-74aa416c5ec2442a9a63de26ff54d828
Source dataset
uspto-grants-1989_07
Patent number
US04845216

Reaction notes

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