Potassium Carbonate → 1,3-Di-tert-butyl-1H-pyrazol-5-amine

HRID 2356851ノート

反応式

HRID 2356851 の反応式
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].Cl.[C:11]([NH:15][NH2:16])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[NH2:6][C:5]1[N:15]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:16]=[C:3]([C:2]([CH3:9])([CH3:8])[CH3:1])[CH:4]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 81889tert-Butylhydrazine monohydrochlorideHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

生成物 1

HCID 433814531,3-Di-tert-butyl-1H-pyrazol-5-amine収率 44.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
25 °C

実験手順

A mixture of 12.5 g of 4,4-dimethyl-3-oxopentanenitrile, 25 g of tert-butylhydrazine hydrochloride, and 27.6 g of potassium carbonate in 400 mL of ethanol was refluxed for 24 h. The mixture was cooled to 25° C. and then it was filtered. The solvent was evaporated from the filtrate and the residue was partitioned between ethyl acetate and distilled water. The organic phase washed with brine and dried (MgSO4). The solvent was evaporated at reduced pressure and the residue was dissolved in a small volume of ether. The mixture was diluted with an equal volume of hexanes and then the volume of the solution was reduced by one half by evaporation at reduced pressure. The white solid which precipitated was collected by filtration to give 8.7 g of 5-Amino-1,3-di(tert-butyl)pyrazole 17. 1H-NMR (CDCl3): δ 5.43 (s, 1H), 1.62 (s, 9H), 1.25 (s, 9H).

後処理

  1. temperaturewas refluxed for 24 h
  2. filtrationit was filtered
  3. customThe solvent was evaporated from the filtrate
  4. customthe residue was partitioned between ethyl acetate
  5. distillationdistilled water
  6. washThe organic phase washed with brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated at reduced pressure
  9. dissolutionthe residue was dissolved in a small volume of ether
  10. additionThe mixture was diluted with an equal volume of hexanes
  11. customthe volume of the solution was reduced by one half by evaporation at reduced pressure
  12. customThe white solid which precipitated
  13. filtrationwas collected by filtration

出典と根拠

ORDレコード
ord-3c27be0f019648dc9314ff7fa9ae6076
出典データセット
uspto-grants-2010_07
特許番号
US07759382B2

反応ノート

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