Acetic Acid → Zinc copper couple

HRID 619928ノート

反応式

HRID 619928 の反応式
S([O-])([O-])(=O)=O.[Cu+2:6].[Zn:7].[CH2:8]([S:15][C:16]1[N:26]=[C:19]2[N:20]=[C:21]([Cl:25])[CH:22]=[C:23](Cl)[N:18]2[N:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)(=O)C>O.CO.O1CCCC1>[Cu:6].[Zn:7].[CH2:8]([S:15][C:16]1[N:26]=[C:19]2[N:20]=[C:21]([Cl:25])[CH:22]=[CH:23][N:18]2[N:17]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

9

反応物 4

HCID 176Acetic AcidHCID 23994ZincHCID 24462Copper SulfateHCID 10519059HCID 10519059、化合物

生成物 2

HCID 10290809Zinc copper coupleHCID 10516623HCID 10516623、化合物

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A zinc-copper couple was prepared following the procedure of Bradley (J. Org. Chem. 31, 626 (1966)) by stirring 1.0 g of copper sulfate in 20 ml of water with 15.0 g of zinc dust for 2 hours. The couple was collected by filtration, washed with acetone and dried overnight under vacuum at 100° C. To a solution of 33.0 g (106 mmol) of 2-benzylthio-5,7-dichloro-1,2,4-triazolo[1,5-a]pyrimidine in 12.5 ml (213 mmol) of acetic acid, 50 ml of methanol and 300 ml of tetrahydrofuran was added 20.5 g of Zn-Cu couple. The mixture was stirred overnight at 22°-23° C. When the reaction was complete (TLC analysis) the reaction mixture was filtered through celite and the filtrate was concentrated by evaporation at reduced pressure. The residue was triturated with hexane to separate a solid. The solid was collected by filtration to yield the desired product as 26.5 g (92%) of orange solid, m.p. 125°-127° C. IR and 1H NMR spectra were in agreement with the assigned structure.

後処理

  1. filtrationThe couple was collected by filtration
  2. washwashed with acetone
  3. customdried overnight under vacuum at 100° C
  4. filtrationwas filtered through celite
  5. concentrationthe filtrate was concentrated by evaporation at reduced pressure
  6. customThe residue was triturated with hexane
  7. customto separate a solid
  8. filtrationThe solid was collected by filtration

出典と根拠

ORDレコード
ord-c337e20b6cf644e3b75ede7e7c03c4eb
出典データセット
uspto-grants-1989_04
特許番号
US04818273

反応ノート

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