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Water → 1-cyclohexanesulfonyl-3-(1-methyl-1,2,3,6-tetrahydropyridine-4-yl) 5-nitro-1H-indole

HRID 1441717
ノート
印刷プレビュー

反応式

HRID 1441717 の反応式
[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH:8]=[C:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=3)[NH:12][CH:11]=2)[CH2:6][CH2:5]1.[CH:22]1([S:28](Cl)(=[O:30])=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.O>CN(C)C=O>[CH:22]1([S:28]([N:12]2[C:13]3[C:18](=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)[C:10]([C:7]3[CH2:6][CH2:5][N:4]([CH3:3])[CH2:9][CH:8]=3)=[CH:11]2)(=[O:30])=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 237554Cyclohexanesulfonyl chlorideHCID 113343733-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole

生成物 1

HCID 115242241-cyclohexanesulfonyl-3-(1-methyl-1,2,3,6-tetrahydropyridine-4-yl) 5-nitro-1H-indole収率 57.2%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

468 mg (9.8 mMol) of 50% sodium hydride in oil were added at 0° C. to a solution of 1.0 g (3.9 mMol) of 3-(1-methyl-1,2,3,6-tetrahydropyridine-4-yl)-5-nitro-1H-indole in 50 ml of anhydrous dimethylformamide, and the mixture was left to stir for 30 minutes. Then 2.14 g of cyclohexanesulfonyl chloride were added, and the stirring continued for 3 hours at room temperature. Water was added and evaporated to dryness. The resulting crude was treated with sodium bicarbonate and was extracted with chloroform. The organic phase was dried with anhydrous sodium sulfate and evaporated to dryness; the resulting solid was purified by chromatography, obtaining 900 mg (57%) of 1-cyclohexanesulfonyl-3-(1-methyl-1,2,3,6-tetrahydropyridine-4-yl)-5-nitro-1H-indole as a yellow solid.

後処理

  1. waitthe mixture was left
  2. waitthe stirring continued for 3 hours at room temperature
  3. customevaporated to dryness
  4. additionThe resulting crude was treated with sodium bicarbonate
  5. extractionwas extracted with chloroform
  6. dry with materialThe organic phase was dried with anhydrous sodium sulfate
  7. customevaporated to dryness
  8. customthe resulting solid was purified by chromatography

出典と根拠

ORDレコード
ord-cda83c00277848d899ff7b2e0a42eb21
出典データセット
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07655690B2

反応ノート

読み込み中…

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