HCID 21495122, compound → 1-{[(2-Bromophenyl)sulfanyl]methyl}pyridin-2(1H)-imine

HRID 1731128Notes

Reaction equation

HRID 1731128 reaction equation
[Cl-].[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N+:4]=1[CH2:9][S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Br:17]>CC(O)C>[Br:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[S:10][CH2:9][N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]1=[NH:2]

Participants

3

Reactant 1

HCID 21495122HCID 21495122, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 2.05 g of sodium 2-propoxide in 200 ml of 2-propanol is added 8.3 g of 2-amino-1-[[(o-bromophenyl)thio]methyl]pyridinium chloride, and the mixture is stirred and heated under reflux for about 5 hours. During this time the flocculent sodium 2-propoxide is replaced by a granular precipitate. The mixture is filtered hot, the insoluble solid is washed repeatedly with warm 2-propanol, and the combined filtrate and washings are concentrated to a volume of about 25 ml in vacuo. The solution is cooled, the solid that separates is filtered, and then is recrystallized from cyclohexane to give 1-[(o-bromophenylthio)methyl] -2-iminopyridine.

Workup

  1. temperatureheated
  2. temperatureunder reflux for about 5 hours
  3. filtrationThe mixture is filtered hot
  4. washthe insoluble solid is washed repeatedly with warm 2-propanol
  5. concentrationthe combined filtrate and washings are concentrated to a volume of about 25 ml in vacuo
  6. temperatureThe solution is cooled
  7. filtrationthe solid that separates is filtered
  8. customis recrystallized from cyclohexane

Sources & evidence

ORD record
ord-2a8e85cf7378499484dde123a4b60fbb
Source dataset
uspto-grants-1976_11
Patent number
US03995042

Reaction notes

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