2-(Ethoxymethylene)propanedinitrile → 5-Amino-1-[2-(trifluoromethyl)phenyl]pyrazole-4-carbonitrile

HRID 1098138

反応式

HRID 1098138 の反応式
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].C(O[CH:16]=[C:17]([C:20]#[N:21])[C:18]#[N:19])C>CO>[NH2:21][C:20]1[N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:11])([F:12])[F:1])[N:10]=[CH:16][C:17]=1[C:18]#[N:19]

参加物

4

反応物 2

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 5208002-(Trifluoromethyl)phenylhydrazine

生成物 1

HCID 121505595-Amino-1-[2-(trifluoromethyl)phenyl]pyrazole-4-carbonitrile収率 100%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
0 °C

実験手順

(2-(Trifluoromethyl)phenyl)hydrazine (CAS no. 365-34-4) (10.0 g, 56.77 mmol) was dissolved in MeOH (150 mL) under nitrogen at 0° C. 2-(ethoxymethylene)malononitrile (6.93 g, 56.77 mmol) added portionwise over 2 mins and the mixture stirred at ˜0° C. for 0.5 hours. The reaction was heated at reflux for 2 hours. Further methanol (15 mL) was added to aid mobility. The mixture was allowed to cool and was evaporated to give the product (14.3 g, 100%) which was used without further purification. 1H NMR (400 MHz, DMSO) δ 6.63 (2H, s), 7.53 (1H, d), 7.73 (1H, s), 7.74-7.77 (1H, m), 7.82-7.86 (1H, m), 7.91-7.94 (1H, m); m/z (ESI+) (M+H)+=253; HPLC tR=1.60 min.

後処理

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 hours
  3. temperatureto cool
  4. customwas evaporated

出典と根拠

ORDレコード
ord-a5125445c2724704991912a9533bfdad
出典データセット
uspto-grants-2012_03
特許番号
US08143263B2

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