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

HRID 1419691노트

반응식

HRID 1419691 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ad548d99a90e4284a18690d849adb848
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05888941

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