Dimethylformamide → 3,5-Diisopropyl salicylamide

HRID 1272264ノート

反応式

HRID 1272264 の反応式
[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]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 305433,5-Diisopropylsalicylic acidHCID 65578Oxalyl chloride

生成物 1

HCID 184569023,5-Diisopropyl salicylamide収率 40%

実験手順

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:

後処理

  1. temperatureThe reaction mixture was refluxed for 1 hour, whereupon the solvent
  2. customthe excess of oxalyl-chloride were removed under reduced pressure
  3. dissolutionThe obtained oily product was dissolved in dichloromethane (50 mL)
  4. additionammonia gas was introduced into reaction mixture
  5. temperatureunder cooling
  6. additionThe solution was diluted with water
  7. dry with materialafter drying with sodium sulfate
  8. customthe organic layer was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-b34348152e9d47119d1b4899d5d6788c
出典データセット
uspto-grants-2007_04
特許番号
US07208518B2

反応ノート

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