p-Toluenesulfonic acid → N-isobutyl-3-methylphthalimide

HRID 733260

反応式

HRID 733260 の反応式
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:5]([O:7][C:8](=[O:9])[C:3]=12)=O.[CH2:13]([NH2:17])[CH:14]([CH3:16])[CH3:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:13]([N:17]1[C:8](=[O:9])[C:3]2=[C:2]([CH3:1])[CH:12]=[CH:11][CH:10]=[C:4]2[C:5]1=[O:7])[CH:14]([CH3:16])[CH3:15]

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 6558IsobutylamineHCID 985004-Methyl-1,3-isobenzofurandione

生成物 1

HCID 22025457N-isobutyl-3-methylphthalimide

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
140 °C

実験手順

N-Isobutyl-3-methylphthalimide is prepared as described in Example 2, starting with 5.0 g of 3-methylphthalic anhydride, 3.0 cm3 of isobutylamine and a catalytic amount of para-toluenesulfonic acid in 50 cm3 of toluene. The reaction mixture is heated at a temperature in the region of 140° C. for 2.5 hours and then stirred at a temperature in the region of 20° C. for 16 hours. The reaction mixture is concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is taken up in dichloromethane and washed twice with saturated aqueous sodium bicarbonate solution. The organic phase is separated out after settling has taken place, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 6.0 g of N-isobutyl-3-methylphthalimide are thus obtained in the form of a caramel-colored oil, Rf=0.76 (thin layer chromatography on silica gel, eluent: dichloromethane).

後処理

  1. customN-Isobutyl-3-methylphthalimide is prepared
  2. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  3. washwashed twice with saturated aqueous sodium bicarbonate solution
  4. customThe organic phase is separated out after settling
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

出典と根拠

ORDレコード
ord-952dde3d152447d9bb281d8fcc8ee311
出典データセット
uspto-grants-2009_09
特許番号
US07589117B2

関連ノート

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