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

HRID 494470노트

반응식

HRID 494470 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ddd66ac5223c4ff697e3cb7098c32d74
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538105B2

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