Potassium Carbonate → HCID 12235834, compound

HRID 1076654Notes

Reaction equation

HRID 1076654 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]=1Br.C(=O)([O-])[O-].[K+].[K+]>[Cu].C(O)CC>[CH:15]1[C:16]2[N:2]=[C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][N:4]3[CH2:9][S:10][C:11]=2[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 21495122HCID 21495122, compound

Product 1

HCID 12235834HCID 12235834, compoundYield 110.5%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 10311-PropanolSolvent

Procedure

A mixture of 33.2 g of 2-amino-1-[[(o-bromophenyl)thio]methyl]pyridinium chloride, 27.7 g of anhydrous potassium carbonate, 0.8 g of copper bronze, and 750 ml of n-propanol is heated and stirred, under reflux, for 24 hours, filtered hot, and the filtrate concentrated to dryness in vacuo. The residue is dissolved in 600 ml of ether, and the ether solution is washed, dried, decolorized with Darco, and concentrated to give about 23.7 g of a yellow solid. Recrystallization from cyclohexane-benzene gives about 17.4 g of the named compound, mp about 135-137°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux, for 24 hours
  3. filtrationfiltered hot
  4. concentrationthe filtrate concentrated to dryness in vacuo
  5. dissolutionThe residue is dissolved in 600 ml of ether
  6. washthe ether solution is washed
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-799064d199ad4793a46e1bea8ae9d1ae
Source dataset
uspto-grants-1976_05
Patent number
US03957799

Reaction notes

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