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

HRID 398780노트

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HRID 398780 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
25 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4e9571c6818c42ff8b1af6eb8bad4f6b
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05817656

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