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

HRID 1444668ノート

反応式

HRID 1444668 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

実験手順

4-[(Methoxymethoxy)methyl]-2-nitrothiophene-3-sulfonamide (1.8 g, 6.4 mmol) was reacted with iron powder (1.43 g, 4 equivalents) in acetic acid (70 mL) at 50° C. for 7.5 hours then concentrated under reduced pressure. A slurry of the residue in 5% methanol/dichloromethane (60 mL) and water (6 mL) was filtered through silica gel (20 g) and further rinsed with 5% methanol/dichloromethane (300 mL). The filtrate was concentrated under reduced pressure and the residue purified by flash chromatography on silica gel using a Biotage-12s column eluting with 2.5:97.5 methanol: dichloromethane to give 2-amino -4-[(methoxymethoxy)methyl]thiophene-3-sulfonamide (1 g, 62%). 1H NMR (300 MHz, DMSO-d6) δ ppm 3.30 (s, 3H), 4.53 (s, 2H), 4.66 (s, 2H), 6.28 (s, 1H), 6.61 (s, 2H), 6.94 (s, 2H).

後処理

  1. concentrationthen concentrated under reduced pressure
  2. filtrationA slurry of the residue in 5% methanol/dichloromethane (60 mL) and water (6 mL) was filtered through silica gel (20 g)
  3. washfurther rinsed with 5% methanol/dichloromethane (300 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue purified by flash chromatography on silica gel using a Biotage-12s column
  6. washeluting with 2.5:97.5 methanol

出典と根拠

ORDレコード
ord-4247dab690824e7e9947e4b6f90796e8
出典データセット
uspto-grants-2010_02
特許番号
US07662958B2

反応ノート

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