Isatoic Anhydride → HCID 9856484、化合物

HRID 1743740ノート

反応式

HRID 1743740 の反応式
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=[O:3].[H-].[Na+].[CH:15]1([CH2:21]Br)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(OCC)(=O)C>CN(C)C(=O)C.O>[CH:15]1([CH2:21][N:6]2[C:5](=[O:12])[O:4][C:2](=[O:3])[C:1]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:7]23)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

参加物

7

反応物 4

HCID 8359Isatoic AnhydrideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 137636Cyclohexane, (bromomethyl)-

生成物 1

HCID 9856484HCID 9856484、化合物収率 23.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
60 °C

実験手順

815 mg (5 mmol) of isatoic acid anhydride is dissolved in 15 ml of N,N-dimethylacetamide and mixed under cover gas and in a moisture-free environment with 220 mg (5.5 mmol) of sodium hydride (60% dispersion in mineral oil). It is heated for 1 hour to 60° C. After cooling, 885 mg (5 mmol) of cyclohexylmethyl bromide is added, and the batch is heated to 60° C. for 4 hours. It is then diluted with water to 60 ml and shaken out three times with ethyl acetate. The combined organic phase is washed with water, dried, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with hexane:ethyl acetate=1:1 as an eluant. 300 mg of N-cyclohexylmethylisatoic acid anhydride is obtained.

後処理

  1. temperatureIt is heated for 1 hour to 60° C
  2. temperatureAfter cooling
  3. washThe combined organic phase is washed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe residue is chromatographed on silica gel with hexane

出典と根拠

ORDレコード
ord-429481f4452e47fcb5b93c1fc6f8d9c8
出典データセット
uspto-grants-2006_03
特許番号
US07012081B2

反応ノート

読み込み中…