4-[(Methoxymethoxy)methyl]-2-nitro-3-thiophenesulfonamide → 2-Amino-4-[(methoxymethoxy)methyl]-3-thiophenesulfonamide

HRID 494470ノート

反応式

HRID 494470 の反応式
[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]1[C:7]([S:14]([NH2:17])(=[O:16])=[O:15])=[C:8]([N+:11]([O-])=O)[S:9][CH:10]=1>C(O)(=O)C.[Fe]>[NH2:11][C:8]1[S:9][CH:10]=[C:6]([CH2:5][O:4][CH2:3][O:2][CH3:1])[C:7]=1[S:14]([NH2:17])(=[O:15])=[O:16]

参加物

4

反応物 1

HCID 670640524-[(Methoxymethoxy)methyl]-2-nitro-3-thiophenesulfonamide

生成物 1

HCID 574551872-Amino-4-[(methoxymethoxy)methyl]-3-thiophenesulfonamide収率 62%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

反応条件

温度
50 °C

実験手順

A solution of the product of Example 10D (1.8 g, 6.4 mmol) in acetic acid (70 mL) was treated with iron powder (1.43 g, 25.5 mmol), stirred at 50° C. for 7.5 h and concentrated. A mixture of the residue in 5% methanol in dichloromethane (60 mL) and water (6 mL) was filtered through silica gel (20 g), and rinsed with 5% methanol in dichloromethane (300 mL). The filtrate was concentrated in vacuo and the residue was chromatographed on silica gel, eluting with methanol in dichloromethane to give the title compound (1 g, 62%). 1H NMR (300 MHz, DMSO-d6): δ 6.94 (s, 2 H), 6.61 (s, 2 H), 6.28 (s, 1 H), 4.66 (s, 2 H), 4.53 (s, 2 H), 3.30 (s, 3 H).

後処理

  1. concentrationconcentrated
  2. additionA mixture of the residue in 5% methanol in dichloromethane (60 mL)
  3. filtrationwater (6 mL) was filtered through silica gel (20 g)
  4. washrinsed with 5% methanol in dichloromethane (300 mL)
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was chromatographed on silica gel
  7. washeluting with methanol in dichloromethane

出典と根拠

ORDレコード
ord-ddd66ac5223c4ff697e3cb7098c32d74
出典データセット
uspto-grants-2009_05
特許番号
US07538105B2

反応ノート

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