2-Methoxyaniline → 4-methoxy-N-(2-methoxyphenyl)benzenesulfonamide

HRID 1503084

反応式

HRID 1503084 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH3:13][O:14][C:15]1[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=1[NH2:17].C(N(CC)CC)C>ClCCl>[CH3:13][O:14][C:15]1[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=1[NH:17][S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10]

参加物

5

反応物 3

HCID 70002-MethoxyanilineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471Triethylamine

生成物 1

HCID 7434174-methoxy-N-(2-methoxyphenyl)benzenesulfonamide収率 75.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-methoxybenzenesulfonyl chloride (5.0 g, 24 mmol) and 2-methoxyaniline (3.0 g, 24 mmol) in dichloromethane (24 mL) at 0° C. was added triethylamine (3.4 mL, 24 mmol) over 10 minutes. The ice bath was removed, and the mixture was stirred for 16 hr. The mixture was diluted with dichloromethane (100 mL) and the combined solution was washed with water (50 mL) and brine (50 mL). The organic solution was dried over MgSO4, filtered, and evaporated, and the crude product was purified by silica gel chromatography (15-60% EtOAc/Hex). Product-containing fractions were pooled, evaporated, and dried under high vacuum to yield 5.3 g (44%) of the product as a tan-colored oil: 1H-NMR (CDCl3) δ 7.70-7.67 (d, 2H), 7.53-7.50 (d, 1H), 7.05-6.99 (m, 2H), 6.91-6.83 (m, 3H), 6.73 (d, 1H), 3.80 (s, 3H), 3.65 (s, 3H).

後処理

  1. customThe ice bath was removed
  2. additionThe mixture was diluted with dichloromethane (100 mL)
  3. washthe combined solution was washed with water (50 mL) and brine (50 mL)
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customthe crude product was purified by silica gel chromatography (15-60% EtOAc/Hex)
  8. customevaporated
  9. customdried under high vacuum

出典と根拠

ORDレコード
ord-27558dc9d9c345b6819f96b64c294c61
出典データセット
uspto-grants-2015_12
特許番号
US09212134B2

関連ノート

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