Ethanol → Benzenesulfonamide, 4-amino-N-[2-(4-morpholinyl)ethyl]-

HRID 1841951

反応式

HRID 1841951 の反応式
[N:1]1([CH2:7][CH2:8][NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O)C.[Cl-].[NH4+]>[Fe].O>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([S:10]([NH:9][CH2:8][CH2:7][N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)(=[O:12])=[O:11])=[CH:18][CH:17]=1

参加物

6

反応物 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 743362N-(2-Morpholin-4-yl-ethyl)-4-nitro-benzenesulfonamide

生成物 1

HCID 120569Benzenesulfonamide, 4-amino-N-[2-(4-morpholinyl)ethyl]-収率 78%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

実験手順

N-(2-Morpholin-4-yl-ethyl)-4-nitro-benzenesulfonamide (0.14 g, 0.45 mmol) was suspended in a 5:1 mixture of ethanol and water (3 ml). To this solution was added iron powder (0.13 g, 2.25 mmol) followed by saturated ammonium chloride solution (0.1 ml) and the mixture was stirred at room temperature for 18 hours. After this time, the reaction mixture was filtered through a pad of celite, the celite was washed with ethanol (10 ml) and ethyl acetate (50 ml) and the solution was concentrated under vacuum. The resulting residue was partitioned between DCM (50 ml) and water (20 ml), the organic layer was separated, dried with MgSO4, filtered and concentrated to afford the title compound (0.1 g, 78% yield) as a brown solid. Tr=0.35 min, m/z (ES+) (M+H)+ 285.

後処理

  1. filtrationAfter this time, the reaction mixture was filtered through a pad of celite
  2. washthe celite was washed with ethanol (10 ml) and ethyl acetate (50 ml)
  3. concentrationthe solution was concentrated under vacuum
  4. customThe resulting residue was partitioned between DCM (50 ml) and water (20 ml)
  5. customthe organic layer was separated
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-4ac684ae0b794e45a27c19eac27c0c9e
出典データセット
uspto-grants-2015_02
特許番号
US08946197B2

関連ノート

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