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

HRID 1098235ノート

反応式

HRID 1098235 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-5d164f5faced4fa98ede5f335c4876e9
出典データセット
uspto-grants-2012_03
特許番号
US08143263B2

反応ノート

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