Triethylamine → 5-Amino-1-(2,6-dichlorophenyl)-3-isopropyl-1H-pyrazole-4-carbonitrile

HRID 507734

반응식

HRID 507734 반응식
Cl[C:2](=[C:6]([C:9]#[N:10])[C:7]#[N:8])[CH:3]([CH3:5])[CH3:4].Cl.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[NH:20][NH2:21].C(N(CC)CC)C>C1COCC1>[NH2:8][C:7]1[N:20]([C:14]2[C:13]([Cl:12])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:19])[N:21]=[C:2]([CH:3]([CH3:5])[CH3:4])[C:6]=1[C:9]#[N:10]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 2723909(2,6-Dichlorophenyl)hydrazine monohydrochlorideHCID 23513711(1-Chloro-2-methylpropylidene)propanedinitrile

생성물 1

HCID 235137165-Amino-1-(2,6-dichlorophenyl)-3-isopropyl-1H-pyrazole-4-carbonitrile수율 62.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (1-chloro-2-methylpropylidene)methane-1,1-dicarbonitrile (9.4 g, 61 mmol) in THF (250 mL) was treated with 2,6-dichlorophenylhydrazine hydrochloride (13.0 g, 61 mmol) followed by triethylamine (12.3 g, 122 mmol). The reaction was then heated to reflux for 18 h. The reaction was then cooled to room temp and partitioned between EtOAc (150 mL) and 1N NaOH (100 mL). The aqueous layer was extracted with EtOAc (2×150 mL) and the combined organic layers were washed with 10% aq. citric acid (150 mL), sat. aq. NaHCO3 (150 mL), and brine (150 mL). The organic layer was dried (MgSO4), filtered, and evaporated. The crude product was recrystallized from EtOAc/hexane to yield the desired pyrazole (11.2 g, 62%).

후처리

  1. temperatureThe reaction was then heated
  2. temperatureto reflux for 18 h
  3. custompartitioned between EtOAc (150 mL) and 1N NaOH (100 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (2×150 mL)
  5. washthe combined organic layers were washed with 10% aq. citric acid (150 mL), sat. aq. NaHCO3 (150 mL), and brine (150 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was recrystallized from EtOAc/hexane

출처 및 근거

ORD 기록
ord-b4aceef08f414459bf21dbec7c101499
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786112B2

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