Iodine → 1-(4-methoxyphenyl)-1H-pyrazole-4-carbonitrile

HRID 1892750ノート

反応式

HRID 1892750 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[C:12]([CH:14]=O)[CH:11]=[N:10]2)=[CH:5][CH:4]=1.II.[OH-].[NH4+:19]>O1CCCC1.S([O-])([O-])(=O)=S.[Na+].[Na+]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[C:12]([C:14]#[N:19])[CH:11]=[N:10]2)=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 807IodineHCID 14923Ammonium HydroxideHCID 41239331-(4-methoxyphenyl)-1H-pyrazole-4-carbaldehyde

生成物 1

HCID 533021171-(4-methoxyphenyl)-1H-pyrazole-4-carbonitrile収率 100%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 24477Sodium Thiosulfate溶媒

実験手順

To a mixture of 1-(4-methoxyphenyl)-1H-pyrazole-4-carbaldehyde (80 mg, 0.54 mmol) in tetrahydrofuran (3 mL) and ammonium hydroxide (3 mL) was added iodine (138 mg, 0.54 mmol). The reaction was stirred at room temperature for 5 hours. The reaction was diluted with saturated sodium thiosulphate (5 mL) and extracted with ethyl acetate (3×10 mL). The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated to give 1-(4-methoxyphenyl)-1H-pyrazole-4-carbonitrile (78 mg, 100%) as a yellow solid. 1H NMR (400 MHz, CDCl3, δ): 8.19 (s, 1H), 7.96 (s, 1H), 7.56 (d, J=9.2 Hz, 2H), 7.01 (d, J=9.2 Hz, 2H), 3.86 (s, 3H).

後処理

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-817bdf81989f43e8958ecb1e57b2ff42
出典データセット
uspto-grants-2013_08
特許番号
US08507533B2

反応ノート

読み込み中…