Sodium Methoxide → 1-{[(2-Bromophenyl)sulfanyl]methyl}pyridin-2(1H)-imine

HRID 1731127Notes

Reaction equation

HRID 1731127 reaction equation
C[O-].[Na+].[Cl-].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N+:7]=1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Br:20]>CO>[Br:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[S:13][CH2:12][N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]1=[NH:5]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 21495122HCID 21495122, compound

Product 1

HCID 218284861-{[(2-Bromophenyl)sulfanyl]methyl}pyridin-2(1H)-imine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5.4 g of sodium methoxide in 400 ml of methanol is added 33.2 g of 2-amino-1-[[(o-bromophenyl)thio]methyl]pyridinium chloride, and the mixture is stirred and heated under reflux for about 5 hours, and filtered while hot. The filtrate is concentrated in vacuo to dryness to give 1-[(o-bromophenylthio)methyl]-2-iminopyridine as a pale yellow crystalline solid after recrystallization from cyclohexane.

Workup

  1. temperatureheated
  2. temperatureunder reflux for about 5 hours
  3. filtrationfiltered while hot
  4. concentrationThe filtrate is concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-f0e986d7eb864e1a89c54209e7350097
Source dataset
uspto-grants-1976_11
Patent number
US03995042

Reaction notes

Loading…