Benzene → HCID 15008720, compound

HRID 1087944Notes

Reaction equation

HRID 1087944 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][CH3:11])[N:5]=1)([CH3:3])=[CH2:2].[Cl:12]N1C(=O)CCC1=O.C1C=CC=CC=1>CCCCCC>[Cl:12][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][CH3:11])[N:5]=1)=[CH2:3]

Participants

5

Reactant 3

HCID 241BenzeneHCID 31398ChlorosuccinimideHCID 22164292HCID 22164292, compound

Product 1

HCID 15008720HCID 15008720, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 14.5 g of 2-isopropenyl-6-methylthiopyridine, 12.9 g of N-chlorosuccinimide and 30 ml of benzene was stirred at 80° C. for 1 hour. After the reaction mixture was cooled to room temperature, n-hexane was added thereto to remove the insoluble matter through filtration. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluted with n-hexane then n-hexane - ethyl acetate 20:1) to obtain 4.3 g of the objective compound.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customto remove the insoluble matter
  3. filtrationthrough filtration
  4. distillationAfter distilling off the solvent
  5. customthe residue was purified by silica gel column chromatography (
  6. washeluted with n-hexane

Sources & evidence

ORD record
ord-8c2d04f017524dd79a5a303e889a128a
Source dataset
uspto-grants-1990_10
Patent number
US04960897

Reaction notes

Loading…