Sodium Hydroxide → 5-amino-1-(2,6-dichlorophenyl)-1H-pyrazole-4-carbonitrile

HRID 1098264

반응식

HRID 1098264 반응식
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[NH:10][NH2:11].[OH-].[Na+].C(O[CH:17]=[C:18]([C:21]#[N:22])[C:19]#[N:20])C>CCOC(C)=O>[NH2:22][C:21]1[N:10]([C:4]2[C:3]([Cl:2])=[CH:8][CH:7]=[CH:6][C:5]=2[Cl:9])[N:11]=[CH:17][C:18]=1[C:19]#[N:20]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 671522-(Ethoxymethylene)propanedinitrileHCID 2723909(2,6-Dichlorophenyl)hydrazine monohydrochloride

생성물 1

HCID 121505555-amino-1-(2,6-dichlorophenyl)-1H-pyrazole-4-carbonitrile수율 94.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

(2,6-Dichlorophenyl)hydrazine hydrochloride (5 g, 23.42 mmol) was partitioned between EtOAc (100 mL) and NaOH (2M, aq) (40 mL). The organic layer separated and washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and concentrated. The resultant oil was suspended in methanol (50 mL) under nitrogen at −5° C. 2-(Ethoxymethylene)malononitrile (2.86 g, 23.42 mmol) added portionwise over 5 mins and the mixture stirred at 0° C. for 30 mins. The reaction mixture was allowed to warm to room temperature and then heated at reflux under nitrogen for 2 hours. The reaction mixture was allowed to cool and evaporated to dryness to afford the product (5.60 g, 94%) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 4.47 (2H, s), 7.43-7.47 (1H, m), 7.51-7.53 (2H, m), 7.73 (1H, s); m/z (ES+) (M+H)+=253; HPLC tR=1.62 min.

후처리

  1. customThe organic layer separated
  2. washwashed with water (50 mL), brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customwas suspended in methanol (50 mL) under nitrogen at −5° C
  7. temperatureto warm to room temperature
  8. temperatureheated
  9. temperatureat reflux under nitrogen for 2 hours
  10. temperatureto cool
  11. customevaporated to dryness

출처 및 근거

ORD 기록
ord-1a364376c0094c1da210d6ca661f6ea5
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143263B2

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