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

HRID 494445ノート

反応式

HRID 494445 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収率 97.1%

試薬・触媒・溶媒 3

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

実験手順

A suspension of the product of Example 2C (7.26 g, 23.57 mmol), ammonium chloride (8.27 g, 155 mmol), and iron powder (8.11 g, 145 mmol) in methanol (188 mL) and water (94 mL) was stirred at reflux for 2 hours. The mixture was filtered while hot through Celite®, and the filter cake was washed with hot methanol (200 mL). The filtrate was concentrated to an approximate volume of 100 mL and then extracted with ethyl acetate (400 mL). The organic layer was washed with water and saturated sodium chloride solution, dried (Na2SO4), filtered through Celite® and concentrated in vacuo to afford the title compound (6.37 g, 97%). 1H NMR (300 MHz, DMSO-d6): δ 7.38 (m, 7 H), 7.22 (m, 2 H), 7.01 (dd, J=8.82, 2.94 Hz, 1 H), 6.76 (d, J=8.82 Hz, 1 H), 5.46 (s, 2 H), 4.98 (s, 2 H).

後処理

  1. temperatureat reflux for 2 hours
  2. filtrationThe mixture was filtered while hot through Celite®
  3. washthe filter cake was washed with hot methanol (200 mL)
  4. concentrationThe filtrate was concentrated to an approximate volume of 100 mL
  5. extractionextracted with ethyl acetate (400 mL)
  6. washThe organic layer was washed with water and saturated sodium chloride solution
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered through Celite®
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d3ab4b57e56c4e99a9b3e7a7ff10e503
出典データセット
uspto-grants-2009_05
特許番号
US07538105B2

反応ノート

読み込み中…