4-Cyanobenzoic acid → 4-[1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]benzonitrile

HRID 584727

反応式

HRID 584727 の反応式
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=O)=[CH:5][CH:4]=1)#[N:2].C(Cl)(=O)C(Cl)=O.[F:18][C:19]([F:33])([F:32])[C:20](=[N:22][NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[NH2:21].C(N(C(C)C)CC)(C)C>ClCCl.O1CCOCC1.CN(C)C=O>[CH3:31][O:30][C:27]1[CH:26]=[CH:25][C:24]([N:23]2[C:7]([C:6]3[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)=[N:21][C:20]([C:19]([F:32])([F:33])[F:18])=[N:22]2)=[CH:29][CH:28]=1

参加物

8

反応物 4

HCID 120874-Cyanobenzoic acidHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 696776222,2,2-trifluoro-N'-(4-methoxyphenyl)ethanehydrazonamide

生成物 1

HCID 102690194-[1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]benzonitrile収率 12.8%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a suspension of 4-cyanobenzoic acid (353 mg, 2.4 mmol) in dichloromethane (3 mL), was added oxalyl chloride (0.209 mL, 2.4 mmol). And then 10 micro-L of dimethylformamide was added to the mixture. The mixture was stirred for 1 hour and the solvent was removed under reduced pressure. The residue was azeotroped with dichloromethane. To the residue, was added 3 mL of dioxane. Then a solution of 2,2,2-trifluoro-N′-(4-methoxyphenyl)ethanehydrazonamide (466 mg, 2 mmol) and diisopropylethylamine (0.418 mL, 2.4 mmol) in 4.5 mL of dioxane was added to the mixture and the mixture was refluxed with stirring for 3.5 hours. The solvent was removed under reduced pressure, and dichloromethane and 0.1 N hydrochloric acid were added to the residue. The organic layer was separated, washed with 0.1 N hydrochloric acid, water, and brine, dried over magnesium sulfate. The crude product was purified by silica gel column chromatography (20:1-10:1 toluene-ethyl acetate). The desired product was rinsed with diisopropyl ether and dried in vacuo to give 4-[1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]benzonitrile (88 mg, 12.8% yield).

後処理

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was azeotroped with dichloromethane
  3. additionTo the residue, was added 3 mL of dioxane
  4. temperaturethe mixture was refluxed
  5. stirringwith stirring for 3.5 hours
  6. customThe solvent was removed under reduced pressure, and dichloromethane and 0.1 N hydrochloric acid
  7. additionwere added to the residue
  8. customThe organic layer was separated
  9. washwashed with 0.1 N hydrochloric acid, water, and brine
  10. dry with materialdried over magnesium sulfate
  11. customThe crude product was purified by silica gel column chromatography (20:1-10:1 toluene-ethyl acetate)
  12. washThe desired product was rinsed with diisopropyl ether
  13. customdried in vacuo

出典と根拠

ORDレコード
ord-d3fb7f8e59d64185ad8ee93601082c07
出典データセット
uspto-grants-2005_08
特許番号
US06927230B2

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