Ammonium Chloride → 2-Amino-5-(benzyloxy)benzenesulfonamide

HRID 601278ノート

反応式

HRID 601278 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:19]([O-])=O)=[C:13]([S:15]([NH2:18])(=[O:17])=[O:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>CO.O.[Fe]>[NH2:19][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][C:13]=1[S:15]([NH2:18])(=[O:16])=[O:17]

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 670638975-(Benzyloxy)-2-nitrobenzenesulfonamide

生成物 1

HCID 670639862-Amino-5-(benzyloxy)benzenesulfonamide

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

The product of Example 304C (3.85 g, 0.0125 mol) was treated with iron powder (4.3 g, 0.077 mol, 6.15 equivalent) and ammonium chloride (4.4 g, 0.082 mol) in methanol (100 mL) and water (50 mL), and stirred at reflux for 1 hour. The hot reaction mixture was filtered through fluted filter paper and washed with hot methanol. The filtrate was concentrated under reduced pressure to a white semi-solid that was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure to give the title compound as a off white solid (2.5 g). 1H NMR (300 MHz, DMSO-d6) δ ppm 4.98 (s, 2 H) 5.46 (s, 2 H) 6.76 (d, J=8.82 Hz, 1 H) 7.01 (dd, J=8.82, 2.94 Hz, 1 H) 7.21 (d, J=2.94 Hz, 1 H) 7.23 (s, 2 H) 7.37 (m, 5 H). ESI m/z (M+H)+279. ESI m/z (M−H)−277.

後処理

  1. temperatureat reflux for 1 hour
  2. filtrationThe hot reaction mixture was filtered
  3. filtrationthrough fluted filter paper
  4. washwashed with hot methanol
  5. concentrationThe filtrate was concentrated under reduced pressure to a white semi-solid
  6. customthat was partitioned between ethyl acetate and water
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-bd108c055e4542cda1711173d60a4a37
出典データセット
uspto-grants-2011_03
特許番号
US07902203B2

反応ノート

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