Diethylhydroxylamine → 2-[5-(N,N-diethylaminooxycarbonylmethylthio)-4-chloro-2-fluorophenyl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione

HRID 128901

反応式

HRID 128901 の反応式
[C:1]([CH2:4][S:5][C:6]1[C:7]([Cl:24])=[CH:8][C:9]([F:23])=[C:10]([N:12]2[C:20](=[O:21])[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[C:13]2=[O:22])[CH:11]=1)([OH:3])=[O:2].[CH2:25]([N:27]([CH2:29][CH3:30])O)[CH3:26]>O1CCCC1>[CH2:25]([N:27]([O:2][C:1]([CH2:4][S:5][C:6]1[C:7]([Cl:24])=[CH:8][C:9]([F:23])=[C:10]([N:12]2[C:20](=[O:21])[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[C:13]2=[O:22])[CH:11]=1)=[O:3])[CH2:29][CH3:30])[CH3:26]

参加物

4

反応物 2

HCID 19463DiethylhydroxylamineHCID 134544942-(5-carboxymethylthio-4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione

生成物 1

HCID 571677982-[5-(N,N-diethylaminooxycarbonylmethylthio)-4-chloro-2-fluorophenyl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione収率 72.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In 20 ml of tetrahydrofuran, 1.85 g of 2-(5-carboxymethylthio-4-chloro -2-fluorophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione was dissolved, to which 0.97 g of N,N'-carbonyldiimidazole was added and the resultant mixture was stirred for 30 minutes at room temperature. To the resultant mixture, 0.53 g of N,N-diethylhydroxylamine was added, and the resultant mixture was stirred for 2 hours at room temperature. After completion of the reaction, the reaction mixture was poured into a saturated saline solution and extracted with ethyl acetate. The extract was washed with a saturated saline solution, dried with anhydrous magnesium sulfate, and evaporated to remove the solvent under reduced pressure. The residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=5:1 to 3:1), which afforded 1.60 g of 2-[5-(N,N-diethylaminooxycarbonylmethylthio)-4-chloro-2-fluorophenyl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione.

後処理

  1. additionwas added
  2. customAfter completion of the reaction
  3. additionthe reaction mixture was poured into a saturated saline solution
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated saline solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customevaporated
  8. customto remove the solvent under reduced pressure
  9. customThe residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=5:1 to 3:1), which

出典と根拠

ORDレコード
ord-ef54eb675b9041be86bab5c4850f5a93
出典データセット
uspto-grants-1995_11
特許番号
US05466663

関連ノート

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