Toluene → HCID 15016280, compound

HRID 2106599Notes

Reaction equation

HRID 2106599 reaction equation
[C:1]([CH:4]([O:6][C:7]1[N:11]=[CH:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:8]=1)[CH3:5])([OH:3])=[O:2].S(Cl)(Cl)=O.[C:26]1(C)C=CC=CC=1>>[CH3:26][O:2][C:1]([CH:4]([O:6][C:7]1[N:11]=[CH:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=2)[N:8]=1)[CH3:5])=[O:3]

Participants

4

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 15016262HCID 15016262, compound

Product 1

HCID 15016280HCID 15016280, compound

Procedure

A 2.5 g portion of the compound of Example 24 was added to 50 ml of toluene, and 3 ml of thionyl chloride was added to the mixture. It was heated under reflux for 2 hours, and was then cooled and evaporated under vacuum. Fifty ml of toluene was added to the residue and was removed under vacuum, and the residue was then taken up in methanol and heated under reflux for 3 hours. The solvent was then removed under vacuum, and the residue was recrystallized from methanol to obtain 2.0 g of the desired product, m.p. 135°-137°.

Workup

  1. additionwas added to the mixture
  2. temperatureIt was heated
  3. temperatureunder reflux for 2 hours
  4. temperaturewas then cooled
  5. customevaporated under vacuum
  6. additionFifty ml of toluene was added to the residue
  7. customwas removed under vacuum
  8. temperatureheated
  9. temperatureunder reflux for 3 hours
  10. customThe solvent was then removed under vacuum
  11. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-2bae296d78984445ab8f3c77f7da5750
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

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