Sodium hydride → Methyl 5-methyl-2-((2-nitrophenyl)amino)thiophene-3-carboxylate

HRID 613244ノート

反応式

HRID 613244 の反応式
[H-].[Na+].[NH2:3][C:4]1[S:5][C:6]([CH3:13])=[CH:7][C:8]=1[C:9]([O:11][CH3:12])=[O:10].F[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22]>O1CCCC1>[N+:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:3][C:4]1[S:5][C:6]([CH3:13])=[CH:7][C:8]=1[C:9]([O:11][CH3:12])=[O:10])([O-:23])=[O:22]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 675878Methyl-2-amino-5-methyl-3-thiophenecarboxylate

生成物 1

HCID 19592005Methyl 5-methyl-2-((2-nitrophenyl)amino)thiophene-3-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
25 °C

実験手順

To a stirred suspension of sodium hydride (2 g) in dry tetrahydrofuran (25 mL) under a nitrogen atmosphere was added a solution of methyl 2-amino-5-methylthiophene-3-carboxy-late (4.8 g, 0.028 mol) and 2-fluoronitrobenzene (4.0 g, 0.025 mol) in dry tetrahydrofuran (30 mL). The mixture was stirred at 25° C. for 20 hours, poured onto ice and partitioned between 2N hydrochloric acid and ethyl acetate. The organic extracts were dried over magnesium sulfate, the solvent was evaporated under reduced pressure and the title compound purified by chromatography on silica gel, eluted with toluene, and crystallized from ethanol (4.1 g).

後処理

  1. additionpoured onto ice
  2. custompartitioned between 2N hydrochloric acid and ethyl acetate
  3. dry with materialThe organic extracts were dried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe title compound purified by chromatography on silica gel
  6. washeluted with toluene
  7. customcrystallized from ethanol (4.1 g)

出典と根拠

ORDレコード
ord-3299c2fca708403090d86af2e13d3214
出典データセット
uspto-grants-1999_12
特許番号
US06008216

反応ノート

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