Dimethylformamide → 3,5-Diisopropyl salicylamide
Reaction equation
[CH:1]([C:4]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:10]=[C:6]([C:7](O)=[O:8])[C:5]=1[OH:16])([CH3:3])[CH3:2].ClCCl.C(Cl)(=O)C(Cl)=O.C[N:27](C=O)C>>[CH:1]([C:4]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:10]=[C:6]([C:7]([NH2:27])=[O:8])[C:5]=1[OH:16])([CH3:3])[CH3:2]Participants
Procedure
To a solution of 3,5-diisopropylsalicylic acid (Aldrich) (10 mmole, 2.2 g) and dichloromethane (20 mL), oxalyl-chloride (Merck) (11.0 mmole, 1.03 mL) and DMF (Aldrich) (80 μL) were added. The reaction mixture was refluxed for 1 hour, whereupon the solvent and the excess of oxalyl-chloride were removed under reduced pressure. The obtained oily product was dissolved in dichloromethane (50 mL) and ammonia gas was introduced into reaction mixture under cooling. The solution was diluted with water and, after drying with sodium sulfate, the organic layer was evaporated under reduced pressure. A yellow residue was recrysatallized from n-hexane, whereat there were obtained 876 mg (40%) of 3,5-diisopropyl salicylamide in the form of a white crystalline product:
Workup
- temperatureThe reaction mixture was refluxed for 1 hour, whereupon the solvent
- customthe excess of oxalyl-chloride were removed under reduced pressure
- dissolutionThe obtained oily product was dissolved in dichloromethane (50 mL)
- additionammonia gas was introduced into reaction mixture
- temperatureunder cooling
- additionThe solution was diluted with water
- dry with materialafter drying with sodium sulfate
- customthe organic layer was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-b34348152e9d47119d1b4899d5d6788c
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07208518B2
Reaction notes
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