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

HRID 655115

반응식

HRID 655115 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

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 portion-wise over 5 mins and the mixture stiffed 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. Alternatively the product was obtained by concentrating the reaction mixture to half volume and allowing the product to crystallise.

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. temperatureheated
  8. temperatureat reflux under nitrogen for 2 hours
  9. temperatureto cool
  10. customevaporated to dryness

출처 및 근거

ORD 기록
ord-f221ea0dd0c545bc9b52b94aa1c4dbad
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071585B2

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