Chloroform → ethyl 5-amino-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate

HRID 1419691ノート

反応式

HRID 1419691 の反応式
C(O[CH:4]=[C:5]([C:11]#[N:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.Cl.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][NH2:22])=[CH:17][CH:16]=1.C(Cl)(Cl)Cl>C(O)C>[NH2:12][C:11]1[N:21]([C:18]2[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=2)[N:22]=[CH:4][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

参加物

5

反応物 3

HCID 6212ChloroformHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester

生成物 1

HCID 4101804ethyl 5-amino-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate収率 48%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of ethyl ethoxymethylenecyanoacetate (3 g, 17.7 mmol) and 4-chlorophenylhydrazine hydrochloride (3.33 g, 18.6 mmol) in ethanol (60 mL) was refluxed for 2 days, following the procedure described in Schmidt, P. et al. Helv.Chim.Acta, 1959, 349. The reaction mixture was then allowed to cool to room temperature, whereupon a precipitate was formed. Cold CHCl3 was added, the precipitate was filtered and washed with more CHCl3. The filtrate and the washings were evaporated to dryness, precipitated with ether, filtered and dried to give ethyl 5-amino-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate (2.25 g, 48%) as a white solid: mp 150°-156° C.; 1H NMR (80 MHz, CDCl3) δ (TMS) 7.77 (s, 1H, pyrazole), 7.48 (s, 4H, arom), 4.30 (q, J=7, 2H, OCH2), 1.36 (t, J=7, 3H, OCH2CH3). Analysis calculated for C12H12ClN3O2 : C 54.25; H 4.55; N 15.81. Found: C 54.77; H 4.49; N 15.65.

後処理

  1. customwas formed
  2. filtrationthe precipitate was filtered
  3. washwashed with more CHCl3
  4. customThe filtrate and the washings were evaporated to dryness
  5. customprecipitated with ether
  6. filtrationfiltered
  7. customdried

出典と根拠

ORDレコード
ord-ad548d99a90e4284a18690d849adb848
出典データセット
uspto-grants-1999_03
特許番号
US05888941

反応ノート

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