Toluene → HCID 15016278, compound

HRID 2106597Notes

Reaction equation

HRID 2106597 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)[CH:29]=CC=C[CH:25]=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][CH:24]([CH3:29])[CH3:25])=[O:2])[CH3:5])=[N:8]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 53652481HCID 53652481, compound

Product 1

HCID 15016278HCID 15016278, compound

Procedure

Three g of the compound of Example 23 was added to 50 ml of toluene, and 5 ml of thionyl chloride was then added. The mixture was heated under reflux for 2 hours, and was then cooled and evaporated under vacuum. Fifty ml of additional toluene was added and removed under vacuum, and then 50 ml of isopropanol was added to the residue. The mixture was heated under reflux for 2 hours, and was then cooled and evaporated under vacuum. The residue was recrystallized from isopropanol to obtain 2.6 g of the desired product, m.p. 55°-57°.

Workup

  1. additionwas then added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. temperaturewas then cooled
  5. customevaporated under vacuum
  6. additionFifty ml of additional toluene was added
  7. customremoved under vacuum
  8. addition50 ml of isopropanol was added to the residue
  9. temperatureThe mixture was heated
  10. temperatureunder reflux for 2 hours
  11. temperaturewas then cooled
  12. customevaporated under vacuum
  13. customThe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-e22c4fb2aeef467c86c52eab31b9992d
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

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