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

HRID 507734

反応式

HRID 507734 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-b4aceef08f414459bf21dbec7c101499
出典データセット
uspto-grants-2010_08
特許番号
US07786112B2

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