2-(Ethoxymethylene)propanedinitrile → 5-amino-1-(2,3-dichlorophenyl)-1H-pyrazole-4-carbonitrile

HRID 1098235노트

반응식

HRID 1098235 반응식
Cl.[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[NH:10][NH2:11].C(O[CH:15]=[C:16]([C:19]#[N:20])[C:17]#[N:18])C.ClC1C(Cl)=CC=CC=1NN>CO>[NH2:20][C:19]1[N:10]([C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([Cl:9])[C:3]=2[Cl:2])[N:11]=[CH:15][C:16]=1[C:17]#[N:18]

참가 물질

5

반응물 3

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 600691(2,3-Dichlorophenyl)hydrazineHCID 122765722,3-Dichlorophenylhydrazine HCl

생성물 1

HCID 27972505-amino-1-(2,3-dichlorophenyl)-1H-pyrazole-4-carbonitrile수율 100%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

(2,3-Dichlorophenyl)hydrazine hydrochloride (CAS no. 21938-47-6) (6.06 g, 28.4 mmol) was partitioned between EtOAc and 2M NaOH. Separated. The organic solution was dried (MgSO4), filtered and reduced to give the free base. 2-(Ethoxymethylene)malononitrile (3.47 g, 28.39 mmol) was added portionwise to a stirred solution of (2,3-dichlorophenyl)hydrazine in MeOH (50 mL), under nitrogen at 5° C. The resulting solution was allowed to stir for a further 1 hour. The reaction mixture was then heated to reflux and was stirred for 3 hours. The reaction mixture was allowed to cool to ambient temperature, then was evaporated to afford the product (7.19 g, 100%) which was used without further purification. 1H NMR (400 MHz, DMSO) δ 6.75 (2H, s), 7.48-7.53 (2H, m), 7.77 (1H, s), 7.79-7.84 (1H, m).

후처리

  1. custom21938-47-6) (6.06 g, 28.4 mmol) was partitioned between EtOAc and 2M NaOH
  2. customSeparated
  3. dry with materialThe organic solution was dried (MgSO4)
  4. filtrationfiltered
  5. customto give the free base
  6. temperatureThe reaction mixture was then heated
  7. temperatureto reflux
  8. stirringwas stirred for 3 hours
  9. customwas evaporated

출처 및 근거

ORD 기록
ord-5d164f5faced4fa98ede5f335c4876e9
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143263B2

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