Thionyl Chloride → HCID 22403871, compound

HRID 259857Notes

Reaction equation

HRID 259857 reaction equation
[C:1]([O:4][C:5]1[C:13]([CH:14]([CH3:16])[CH3:15])=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[CH:17]([CH3:19])[CH3:18])(=[O:3])[CH3:2].S(Cl)([Cl:22])=O>CN(C=O)C>[C:1]([O:4][C:5]1[C:13]([CH:14]([CH3:16])[CH3:15])=[CH:12][C:8]([C:9]([Cl:22])=[O:10])=[CH:7][C:6]=1[CH:17]([CH3:19])[CH3:18])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22403924HCID 22403924, compound

Product 1

HCID 22403871HCID 22403871, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 4-acetoxy-3,5-diisopropylbenzoic acid (634 mg), thionyl chloride (3 ml) and DMF (1 drop) was refluxed for 40 minutes, concentrated and evaporated to obtain 4-acetoxy-3,5-diisopropylbenzoyl chloride. The resultant was dissolved in dichloromethane (20 ml), to which 3-amino-4-(2-chlorophenyl)-6,8-dimethylquinoline (566 mg) and triethylamine (0.30 ml) were added. Thus obtained solution was stirred at room temperature for one night. After dilution with water, the solution was extracted with dichloromethane. The dichloromethane layer was washed with 2N-hydrochloric acid and water, and then dried (MgSO4). The solvent was removed and the residue was recrystallized from ethanol to obtain 3-(4-acetoxy-3,5-diisopropylbenzamido)-4-(2-chlorophenyl)-6,8-dimethylquinoline (815 mg, 77.0%) as colorless prisms.

Workup

  1. temperaturewas refluxed for 40 minutes
  2. concentrationconcentrated
  3. customevaporated

Sources & evidence

ORD record
ord-bb80ec533bd543a19e73ef7050dd4e93
Source dataset
uspto-grants-1996_06
Patent number
US05523407

Reaction notes

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