Toluene → HCID 15016277, compound

HRID 2106596Notes

Reaction equation

HRID 2106596 reaction equation
[C:1]([CH:4]([O:6][C:7]1[N:11]=[CH:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[N:8]=1)[CH3:5])([OH:3])=[O:2].S(Cl)(Cl)=O.[C:24]1(C)C=CC=CC=1>>[Cl:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[N:9]1[CH:10]=[N:11][C:7]([O:6][CH:4]([C:1]([O:3][CH3:24])=[O:2])[CH3:5])=[N:8]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 53652481HCID 53652481, compound

Product 1

HCID 15016277HCID 15016277, compound

Procedure

Three g of the compound of Example 23 was added to 75 ml of toluene and 5 ml of thionyl chloride, and the solution was heated under reflux for 2 hours. It was then cooled and evaporated under vacuum. Fifty ml of toluene was added to the residue, and that solvent was also removed under vacuum. To the residue was then added 50 ml of methanol, and the solution was heated under reflux for 2 hours, cooled and evaporated under vacuum. The residue was recrystallized from toluene to obtain 0.68 g of the desired product, m.p. 74°-75°.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureIt was then cooled
  4. customevaporated under vacuum
  5. additionFifty ml of toluene was added to the residue
  6. customthat solvent was also removed under vacuum
  7. additionTo the residue was then added 50 ml of methanol
  8. temperaturethe solution was heated
  9. temperatureunder reflux for 2 hours
  10. temperaturecooled
  11. customevaporated under vacuum
  12. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-3089ae9bd0334f699c170d5a024e1cb7
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

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