Benzoyl chloride → Phenyl-n-(3-phenyl(1h-indazol-5-yl))carboxamide

HRID 1272738

反応式

HRID 1272738 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C.C(N(CC)CC)C>[C:18]1([C:17]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][N:6]=[C:5]3[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

5

反応物 2

HCID 7412Benzoyl chlorideHCID 224801043-Phenyl-1H-indazol-5-amine

生成物 1

HCID 20789113Phenyl-n-(3-phenyl(1h-indazol-5-yl))carboxamide収率 8%

試薬・触媒・溶媒 2

HCID 8471Triethylamine触媒HCID 6342Acetonitrile溶媒

実験手順

To a mixture of 5-amino-3-phenyl-1H-indazole (190 mg, 0.909 mmol) in acetonitrile (6 mL) was added benzoyl chloride (123 mg, 0.909 mmol). The solution was allowed to reflux for three hours. Triethylamine (3 drops) was added over a period of one hour while reflux continued for an additional hour. The solution was condensed and distilled water was added. The reaction mixture was extracted with ethyl acetate. The organics were dried using sodium sulfate, and condensed to give a solid. The solid was purified using chromatography (SiO2, 30–45% ethyl acetate/hexanes) to give the title compound (20 mg, 8% yield). 1H NMR (DMSO-d6) δ 13.40 (br s, 1H), 10.32 (s, 1H), 8.56 (s, 1H), 7.96 (m, 4H), 7.75 (d, 1H), 7.55 (m, 6H), 7.39 (t, 1H); ES-MS (m/z) 314 [M+1]+.

後処理

  1. temperatureto reflux for three hours
  2. temperaturewhile reflux
  3. waitcontinued for an additional hour
  4. customcondensed
  5. distillationdistilled water
  6. additionwas added
  7. extractionThe reaction mixture was extracted with ethyl acetate
  8. customThe organics were dried
  9. customsodium sulfate, and condensed
  10. customto give a solid
  11. customThe solid was purified

出典と根拠

ORDレコード
ord-21ffdbc5cd51486486fac2ac3ff28473
出典データセット
uspto-grants-2007_04
特許番号
US07208513B2

関連ノート

読み込み中…