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Potassium Carbonate → N-(4-(benzyloxy)pyridin-3-yl)-N-(methylsulfonyl)methane sulfonamide

HRID 2068416
ノート
印刷プレビュー

反応式

HRID 2068416 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[N+:15]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[N:15]([S:25]([CH3:24])(=[O:27])=[O:26])[S:25]([CH3:24])(=[O:27])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 127165204-(Benzyloxy)-3-nitropyridine

生成物 1

HCID 67217559N-(4-(benzyloxy)pyridin-3-yl)-N-(methylsulfonyl)methane sulfonamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

4-(Benzyloxy)-3-nitropyridine (14 g, 69.8 mmol, 1 eq) was dissolved in dichloromethane and cooled to 0° C. Then added TEA (29.2 ml, 209.6 mmol, 3 eq), followed by the addition of potassium carbonate (9.96 g, 69.8 mmol, 1 eq) at 0° C. and stirred for 15 minutes. Methane sulfonyl chloride (20 g, 174 mmol, 2.5 eq) was added slowly at 0° C. to the above mixture and stirred for 14 h. After the completion of reaction, monitored by TLC, the reaction mixture was diluted with water and organic layer was separated. Water layer was extracted twice with 200 ml of dichloromethane, and the combined dichloromethane mixture was washed with water (500 ml) and brine (500 ml). The organic solution was concentrated under vacuum to yield the pure product. Yield: 19.5 g (78%). 1HNMR (400 MHz, DMSO-d6): δ 3.47 (S, 6H), 5.35 (s, 2H), 7.32 (d, J=5.76 Hz, 1H), 7.40-7.49 (m, 3H), 7.51 (t, J=4.12 Hz, 2H), 8.52 (d, J=5.68 Hz, 1H), 8.57 (s, 1H).

後処理

  1. stirringstirred for 14 h
  2. customAfter the completion of reaction
  3. customwas separated
  4. extractionWater layer was extracted twice with 200 ml of dichloromethane
  5. washthe combined dichloromethane mixture was washed with water (500 ml) and brine (500 ml)
  6. concentrationThe organic solution was concentrated under vacuum
  7. customto yield the pure product

出典と根拠

ORDレコード
ord-f065993b0f92422a8b0018797ab2ea5f
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08293909B2

反応ノート

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