Diphenyl disulfide → HCID 12851841, compound

HRID 1156899Notes

Reaction equation

HRID 1156899 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][N:9]=2)=[CH:4][CH:3]=1.C1(SSC2C=CC=CC=2)C=CC=CC=1>C1CCCCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 13436Diphenyl disulfideHCID 12851825HCID 12851825, compound

Product 1

HCID 12851841HCID 12851841, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

1-(4-Methylphenyl)-5-chloro-3,4-dihydroisoquinoline (29 g) and 24.7 g of diphenyl disulfide were reacted over an oil bath at 220° C. The reaction mixture was dissolved in cyclohexane, and extracted with a 4 N aqueous solution of hydrochloric acid. The aqueous layer was neutralized with an aqueous solution of sodium hydroxide. The resulting oily product was extracted with benzene, washed in water, and dried. The solvent was distilled off, and the residue was recrystallized from benzene to afford 22.5 g of 1-(4-methylphenyl)-5-chloroisoquinoline as colorless needles having a melting point of 88.6° to 89.1° C.

Workup

  1. extractionextracted with a 4 N aqueous solution of hydrochloric acid
  2. extractionThe resulting oily product was extracted with benzene
  3. washwashed in water
  4. customdried
  5. distillationThe solvent was distilled off
  6. customthe residue was recrystallized from benzene

Sources & evidence

ORD record
ord-94af7538df9847f88417197c86cb9a40
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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