Sulfuric Acid → Tert-butyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylate

HRID 377637ノート

反応式

HRID 377637 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([OH:23])=[O:22])[C:9]=2[CH3:24])=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:30][C:31]([CH3:33])=[CH2:32]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([O:23][C:31]([CH3:33])([CH3:32])[CH3:30])=[O:22])[C:9]=2[CH3:24])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 15194215-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid

生成物 1

HCID 19356241Tert-butyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylate

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
-10 °C

実験手順

A solution of 5 g of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid in 35 ml of dioxane is introduced into a 250 ml autoclave and then cooled to -10° C. 2 ml of concentrated H2SO4 and 70 ml of 2-methylpropene, cooled to -10° C., are then added and the autoclave is closed, allowed to warm up to RT and then heated at 40° C. for 18 hours, with vigorous stirring. After cooling to RT, the reaction mixture is concentrated under vacuum, the residue is extracted with DCM, the organic phase is washed with water, with 5% Na2CO3 solution and with saturated NaCl solution and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a toluene/AcOEt mixture (from 90/10 to 80/20; v/v) as the eluent to give 3.15 g of the expected product, m.p.=112° C.

後処理

  1. additionare then added
  2. customthe autoclave is closed
  3. temperatureto warm up to RT
  4. temperatureheated at 40° C. for 18 hours, with vigorous stirring
  5. temperatureAfter cooling to RT
  6. concentrationthe reaction mixture is concentrated under vacuum
  7. extractionthe residue is extracted with DCM
  8. washthe organic phase is washed with water, with 5% Na2CO3 solution and with saturated NaCl solution
  9. dry with materialdried over MgSO4
  10. customthe solvent is evaporated off under vacuum
  11. customThe residue is chromatographed on silica using a toluene/AcOEt mixture (from 90/10 to 80/20; v/v) as the eluent

出典と根拠

ORDレコード
ord-9129f6b96eff45db94e1d3906d21f3a1
出典データセット
uspto-grants-2000_02
特許番号
US06028084

反応ノート

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