4-Methyl-N-(2-oxo-3-azepanyl)benzenesulfonamide → N-(Azepan-3-yl)-4-methylbenzenesulfonamide

HRID 458620

反応式

HRID 458620 の反応式
O=[C:2]1[CH:8]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([NH:9][S:10]([C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)(=[O:11])=[O:12])[CH2:2]1

参加物

4

反応物 2

HCID 38035924-Methyl-N-(2-oxo-3-azepanyl)benzenesulfonamideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 22508595N-(Azepan-3-yl)-4-methylbenzenesulfonamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

N-(2-Oxoazepan-3-yl)-4-methylbenzenesulfonamide (6A) (4.24 g, 15 mmol) was dissolved in 250 ml of dry THF under a nitrogen atmosphere, and lithium aluminium hydride (1.11 g, 30 mmol) was added slowly. The reaction was heated to reflux for 20 hours and then quenched with water until the effervescence ceased. Solid potassium carbonate was added until a white suspension appeared, and the mixture was allowed to stir for half an hour. The suspension was filtered through celite, which was washed with 3×50 ml of EtOAc. The solvents were evaporated and the residue was dissolved in 100 ml of EtOAc and 100 ml of water. The layers were separated and the aqueous layer was extracted with 2×100 ml of EtOAc. The combined organic layer was washed with brine, dried over sodium sulphate, and evaporated to give compound (6B) as an oil.

後処理

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 20 hours
  3. customquenched with water until the effervescence
  4. additionSolid potassium carbonate was added until a white suspension
  5. filtrationThe suspension was filtered through celite, which
  6. washwas washed with 3×50 ml of EtOAc
  7. customThe solvents were evaporated
  8. dissolutionthe residue was dissolved in 100 ml of EtOAc
  9. customThe layers were separated
  10. extractionthe aqueous layer was extracted with 2×100 ml of EtOAc
  11. washThe combined organic layer was washed with brine
  12. dry with materialdried over sodium sulphate
  13. customevaporated

出典と根拠

ORDレコード
ord-eec6c5143ef04531842b22d66ca66e0e
出典データセット
uspto-grants-2007_03
特許番号
US07192952B2

関連ノート

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