Diethyl Ether → Ethyl 5-(4-aminophenylthio)-4-nitrothiophene-2-carboxylate

HRID 605373노트

반응식

HRID 605373 반응식
Cl[C:2]1[S:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1.C([O-])(=O)C.[Na+].C(OCC)C>C(O)C>[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][C:2]2[S:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 145104-AminothiophenolHCID 517045Sodium AcetateHCID 56763846HCID 56763846, 화합물

생성물 1

HCID 67040833Ethyl 5-(4-aminophenylthio)-4-nitrothiophene-2-carboxylate수율 85%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

The product of Example 430A (1.0 g, 4.244 mmol), 4-aminothiophenol (0.797 g, 6.366 mmol), and anhydrous sodium acetate (1.74 g, 21.22 mmol) were heated in anhydrous ethanol (40 mL) under a nitrogen atmosphere at reflux for 30 minutes. The reaction was cooled to room temperature, partitioned with ethyl acetate (100 mL) and water (50 mL), separated layers, and washed organic phase with water (2×50 mL) and brine (50 mL). The organic extract was dried over sodium sulfate, filtered, and concentrated by rotary evaporation. Trituration of the resulting solid with ethyl ether (2×30 mL) afforded the title compound as a bright yellow solid (1.167 g, 3.598 mmol, 85%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.24 (t, J=7.17 Hz, 3 H) 4.24 (q, J=7.23 Hz, 2 H) 5.94 (s, 2 H) 6.71 (d, J=8.82 Hz, 2 H) 7.35 (d, J=8.46 Hz, 2 H) 8.08 (s, 1 H); MS (ESI+) m/z 325 (M+H)+, MS (ESI−) m/z 323 (M−H)−.

후처리

  1. temperatureat reflux for 30 minutes
  2. custompartitioned with ethyl acetate (100 mL) and water (50 mL)
  3. customseparated layers
  4. washwashed organic phase with water (2×50 mL) and brine (50 mL)
  5. extractionThe organic extract
  6. dry with materialwas dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation

출처 및 근거

ORD 기록
ord-13a78b58b5a9458c8a37068dcc6a64aa
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910595B2

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