ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Oxalyl chloride → N-(2-chloro-6-fluoro-3-hydroxy-phenyl)-2-fluoro-5-(3-fluorophenyl)benzamide

HRID 1771665
ノート
印刷プレビュー

反応式

HRID 1771665 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)(C(Cl)=O)=O.[NH2:24][C:25]1[C:26]([Cl:33])=[C:27]([OH:32])[CH:28]=[CH:29][C:30]=1[F:31].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C.C1COCC1.O>[Cl:33][C:26]1[C:27]([OH:32])=[CH:28][CH:29]=[C:30]([F:31])[C:25]=1[NH:24][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH:9]=[CH:10][C:2]=1[F:1]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 216600263-Amino-2-chloro-4-fluorophenolHCID 463123323',4-Difluoro-[1,1'-biphenyl]-3-carboxylic acid

生成物 1

HCID 89443695N-(2-chloro-6-fluoro-3-hydroxy-phenyl)-2-fluoro-5-(3-fluorophenyl)benzamide収率 26%

試薬・触媒・溶媒 4

HCID 6228
Dimethylformamide
触媒
HCID 962Water溶媒
HCID 6344Dichloromethane溶媒
HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 2-fluoro-5-(3-fluorophenyl)benzoic acid (intermediate III(a)) (478 mg, 2.04 mmol, 1.1 eq) in DCM (9 mL) and DMF (3 drops) at 0° C. was added (COCl)2 (779 mg, 6.14 mmol, 3.3 eq) dropwise. The reaction mixture was stirred at room temperature for 1.5 h, then the solvent removed in vacuo. The residue obtained was dissolved in THF (7 mL) and added dropwise to a mixture of 3-amino-2-chloro-4-fluoro-phenol (intermediate X(f)) (300 mg, 1.86 mmol, 1.0 eq) and NaHCO3 (781 mg, 9.3 mmol, 5.0 eq) in THF (7 mL) at 0° C. After addition was completed, the reaction mixture was warmed to room temperature and stirred overnight. Water was added and the aqueous mixture was extracted with EtOAc. The organic extract was washed with 5% Na2CO3, water and brine, dried (Na2SO4), filtered, evaporated in vacuo and purified by column chromatography (EtOAc:petroleum ether, 3:20 to 1:4) to give the title as a yellow solid compound (180 mg, 26%).

後処理

  1. customthe solvent removed in vacuo
  2. customThe residue obtained
  3. additionAfter addition
  4. temperaturethe reaction mixture was warmed to room temperature
  5. stirringstirred overnight
  6. extractionthe aqueous mixture was extracted with EtOAc
  7. extractionThe organic extract
  8. washwas washed with 5% Na2CO3, water and brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. custompurified by column chromatography (EtOAc:petroleum ether, 3:20 to 1:4)

出典と根拠

ORDレコード
ord-d1d783cf3af84ec08b621292584869a7
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09249085B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート