Water → N-(4-(6-chloropyrazin-2-ylthio)phenyl)cyclopropanecarboxamide

HRID 1668650

反応式

HRID 1668650 の反応式
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].[Cl:16][C:17]1[CH:22]=[N:21][CH:20]=[C:19](Cl)[N:18]=1.O>C1COCC1.C(OCC)(=O)C>[Cl:16][C:17]1[N:18]=[C:19]([S:1][C:2]2[CH:3]=[CH:4][C:5]([NH:8][C:9]([CH:11]3[CH2:12][CH2:13]3)=[O:10])=[CH:6][CH:7]=2)[CH:20]=[N:21][CH:22]=1

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 785042,6-DichloropyrazineHCID 16722082N-(4-mercaptophenyl)cyclopropanecarboxamide

生成物 1

HCID 59343401N-(4-(6-chloropyrazin-2-ylthio)phenyl)cyclopropanecarboxamide収率 72%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of N-(4-mercaptophenyl)cyclopropane carboxamide (16.1 mmol) in THF (25 mL) at 0° C. was added sodium hydride (16.1 mmol) portionwise. Once the addition was complete the resulting solution was stirred at room temperature for 30 min. After this time, the reaction mixture was cooled to 0° C. and a solution of 2,6-dichloropyrazine (13.4 mmol) was added and the resulting mixture stirred at room temperature for 16 h. Water (30 mL) and ethyl acetate (30 mL) were added and the layers separated. The aqueous layer was extracted further with ethyl acetate (2×30 mL), the combined organic layers dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (EtOAc/Petroleum ether, 0-100% gradient EtOAc) to give the title compound (2.95 g, 72%) as a cream coloured solid; 1H NMR (400 MHz, DMSO-d6) δ 0.91 (2H, m), 1.13 (2H, m), 1.54 (1H, m), 7.53 (1H, br s), 7.57 (2H, m), 7.65 (2H, m), 7.96 (1H, s), 8.22 (1H, s); MS (ES+): m/e=306.14 (100%).

後処理

  1. additionOnce the addition
  2. temperatureAfter this time, the reaction mixture was cooled to 0° C.
  3. stirringthe resulting mixture stirred at room temperature for 16 h
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted further with ethyl acetate (2×30 mL)
  6. dry with materialthe combined organic layers dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (EtOAc/Petroleum ether, 0-100% gradient EtOAc)

出典と根拠

ORDレコード
ord-a18b1139f40540fab1a7e916229868e7
出典データセット
uspto-grants-2011_08
特許番号
US07989456B2

関連ノート

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