2-(Ethoxymethylene)propanedinitrile → 5-amino-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazole-4-carbonitrile

HRID 1958386

反応式

HRID 1958386 の反応式
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:12][NH2:13].C[O-].[Na+].C(O[CH:20]=[C:21]([C:24]#[N:25])[C:22]#[N:23])C>CO>[NH2:25][C:24]1[N:12]([C:3]2[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:7][C:2]=2[F:1])[N:13]=[CH:20][C:21]=1[C:22]#[N:23]

参加物

5

反応物 3

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 2782739[2-Fluoro-4-(methylsulfonyl)phenyl]hydrazineHCID 10942334Sodium Methoxide

生成物 1

HCID 218975935-amino-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazole-4-carbonitrile収率 87.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

(2-Fluoro-4-methanesulfonyl-phenyl)-hydrazine (1 g, 4.89 mmol) and sodium methoxide (30 mg, 0.489 mmol) were dissolved in methanol under N2 at room temperature. The mixture was stirred for 10 min and 2-ethoxymethylene-malononitrile (0.6 g, 4.91 mmol) was added. The reaction mixture was stirred for 30 min and then brought to reflux for 2 hours. The solvent was removed under reduced pressure; the residue was suspended in water and extracted with ethyl acetate. The organic layer was washed with water, brine and was dried over sodium sulfate. The solvent was concentrated, affording 5-amino-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazole-4-carbonitrile as a yellow solid (1.2 g, 87.5%). 1H NMR (400 MHz DMSO-d6) δ (ppm): 7.96 (d, 1H); 7.93 (m, 1H); 7.80 (s, 1H); 7.74 (m, 1H); 6.89 (s, 2H); 3.24 (s, 3H). Exact mass calculated for C11H9FN4O2S 280.04, found 281.30 (MH+, 100%).

後処理

  1. stirringThe reaction mixture was stirred for 30 min
  2. temperatureto reflux for 2 hours
  3. customThe solvent was removed under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water, brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationThe solvent was concentrated

出典と根拠

ORDレコード
ord-07fbcaaefe12410fa8e553be7efe6fe7
出典データセット
uspto-grants-2013_04
特許番号
US08410119B2

関連ノート

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