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Sodium Carbonate → N-(2,6-difluoro-3-hydroxy-phenyl)-5-(3-fluorophenyl)-2,3-dimethyl-benzamide

HRID 1771703
ノート
印刷プレビュー

反応式

HRID 1771703 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH3:18])[C:11]([CH3:17])=[C:12]([CH:16]=2)[C:13]([OH:15])=O)[CH:5]=[CH:6][CH:7]=1.C(Cl)(C(Cl)=O)=O.[NH2:25][C:26]1[C:27]([F:34])=[C:28]([OH:33])[CH:29]=[CH:30][C:31]=1[F:32].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.C1COCC1.CCOC(C)=O.O.CN(C=O)C>[F:34][C:27]1[C:28]([OH:33])=[CH:29][CH:30]=[C:31]([F:32])[C:26]=1[NH:25][C:13](=[O:15])[C:12]1[CH:16]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH:9]=[C:10]([CH3:18])[C:11]=1[CH3:17]
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

HCID 10340Sodium CarbonateHCID 65578Oxalyl chlorideHCID 227559833-Amino-2,4-difluorophenolHCID 894435205-(3-Fluorophenyl)-2,3-dimethyl-benzoic acid

生成物 1

HCID 89443837N-(2,6-difluoro-3-hydroxy-phenyl)-5-(3-fluorophenyl)-2,3-dimethyl-benzamide収率 15.7%

試薬・触媒・溶媒 5

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒
HCID 6344Dichloromethane溶媒
HCID 8028Tetrahydrofuran溶媒2 回
HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 5-(3-fluorophenyl)-2,3-dimethyl-benzoic acid (3.82 g, 15.6 mmol, 5.8 eq) in DCM (30 mL) was added (COCl)2 (5.96 g, 46.8 mmol, 17.0 eq) and DMF (0.5 mL). The mixture was stirred at room temperature under N2 for 2 h then the solvent removed in vacuo. The residue obtained was dissolved in THF (10 mL) and added to a mixture of 3-amino-2,4-difluoro-phenol (intermediate X(a)) (0.4 g, 2.75 mmol, 1.0 eq) and Na2CO3 (0.87 g, 8.26 mmol, 3.0 eq) in THF. The reaction was stirred at room temperature overnight then water and EtOAc were added. The organic extract was washed with water, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (DCM:MeOH, 0:1 to 1:50) to give the title compound as a solid (0.16 g, 15%).

後処理

  1. customthe solvent removed in vacuo
  2. customThe residue obtained
  3. stirringThe reaction was stirred at room temperature overnight
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue obtained
  10. customwas purified by column chromatography (DCM:MeOH, 0:1 to 1:50)

出典と根拠

ORDレコード
ord-a528e0cb9a0944e5babf0e96d91e3ea1
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

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