1,3-Dibromopropane → HCID 20427608, compound

HRID 615316Notes

Reaction equation

HRID 615316 reaction equation
[CH2:1]([S:3][C:4]1[NH:5][C:6](=[O:23])[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]=1[C:9]#[N:10])[CH3:2].[H-].[Na+].[Br:26][CH2:27][CH2:28][CH2:29]Br>O1CCOCC1>[Br:26][CH2:27][CH2:28][CH2:29][N:5]1[C:6](=[O:23])[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([C:9]#[N:10])=[C:4]1[S:3][CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 132361792-(Ethylsulfanyl)-5-oxo-4,4-diphenyl-4,5-dihydro-1H-pyrrole-3-carbonitrile

Product 1

HCID 20427608HCID 20427608, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

One dissolves 15.0 g 2-ethylthio-5-oxo-4,4-diphenyl-2-pyrroline-3-carbonitrile in 500 ml abs. dioxan, adds 1.4 g sodium hydride (80%) in white oil) thereto and boils under reflux for one hour. One allows to cool somewhat, adds 100.0 g 1,3-dibromopropane thereto and further boils for 48 hours. Thereafter, the reaction mixture is filtered, the solvent and the excess dibromopropane are distilled off under water pump vacuum and the residue is triturated with diisopropyl ether. One obtains 14.0 g 1-(3-bromopropyl)-2-ethylthio-5-oxo-4,4-diphenyl-2-pyrroline-3-carbonitrile of mp 97° C.

Workup

  1. temperatureunder reflux for one hour
  2. temperatureto cool somewhat
  3. filtrationThereafter, the reaction mixture is filtered
  4. distillationthe solvent and the excess dibromopropane are distilled off under water pump vacuum
  5. customthe residue is triturated with diisopropyl ether

Sources & evidence

ORD record
ord-846fb5838c8b48beb819b2e17b18e5c6
Source dataset
uspto-grants-1985_02
Patent number
US04499089

Reaction notes

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