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氯化亚锡二水合物 → 4-(4-Pyridin-2-yl-[1,2,3]triazol-1-yl)-phenylamine

HRID 1924924
笔记
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反应方程式

HRID 1924924 反应方程式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:12]=[N:11]2)=[CH:6][CH:5]=1)([O-])=O.O.O.[Sn](Cl)Cl>C1COCC1.CCO>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:13]1[N:12]=[N:11][N:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH:14]=1
参与物实验过程后处理来源与证据反应笔记

参与物

4

反应物 2

HCID 61436氯化亚锡二水合物HCID 590229972-[1-(4-Nitro-phenyl)-1H-[1,2,3]triazol-4-yl]-pyridine

产物 1

HCID 590231334-(4-Pyridin-2-yl-[1,2,3]triazol-1-yl)-phenylamine收率 31.4%

试剂、催化剂与溶剂 1

HCID 21873804Tetrahydrofuran ethanol溶剂

实验过程

To a stirred solution of 2-[1-(4-nitro-phenyl)-1H-[1,2,3]triazol-4-yl]-pyridine (0.149 g, 0.556 mmol) in 1:1 THF/EtOH (8 mL) is added tin (II) dichloride dihydrate (0.439 g, 1.95 mmol) and the mixture is stirred at room temperature for 22 hours. The solvent is removed in vacuo and 2N NaOH (3 mL) added to the residue. The mixture is stirred for 1 hour, diluted with water and extracted with DCM (3×40 mL). The organic layers are dried over Na2SO4, filtered and evaporated to give a crude product purified by Isolute FlashSilicaII Cartridge chromatography, eluting with 98:2 DCM:MeOH. The fractions containing the title compound are combined and evaporated to afford the desired compound as a yellow solid (41.4 mg, 31%).

后处理

  1. customThe solvent is removed in vacuo and 2N NaOH (3 mL)
  2. additionadded to the residue
  3. stirringThe mixture is stirred for 1 hour
  4. additiondiluted with water
  5. extractionextracted with DCM (3×40 mL)
  6. dry with materialThe organic layers are dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give a crude product
  10. custompurified by Isolute FlashSilicaII Cartridge chromatography
  11. washeluting with 98:2 DCM
  12. additionThe fractions containing the title compound
  13. customevaporated

来源与证据

ORD记录
ord-8ff26fa2c3fc44e88d3f5470ff6a7ac1
来源数据集
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
专利号
US08178530B2

反应笔记

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