Sodium Pyrosulfite → N-{[6-bromo-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamide

HRID 1878017ノート

反応式

HRID 1878017 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10](CC3C=CC(OC)=CC=3)[C:9](=[O:20])[O:8][C:7]([CH2:25][NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)([C:21]([F:24])([F:23])[F:22])[C:6]=2[CH:36]=1.[N+]([O-])([O-])=O.[NH4+].[Ce].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(#N)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:20])[O:8][C:7]([CH2:25][NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)([C:21]([F:24])([F:23])[F:22])[C:6]=2[CH:36]=1

参加物

6

反応物 3

HCID 656671Sodium PyrosulfiteHCID 44549804N-{[6-bromo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamideHCID 57418452Ammonium cerium-nitrate

生成物 1

HCID 44549926N-{[6-bromo-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamide

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

While stirring a solution of N-{[6-bromo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamide (13.0 g, 22.9 mmol) in acetonitrile (50 mL), an aqueous solution (25 mL) of cerium ammonium nitrate (37.7 g, 68.7 mmol) was added dropwise thereto at room temperature. The reaction solution was stirred at room temperature for 4 hours. Sodium pyrosulfite was added to the reaction solution, and the solution was stirred for 30 minutes and then diluted with ethyl acetate, and the organic layer was separated. The organic layer was washed sequentially with water and saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The resulting residue was crystallized from ethyl acetate-heptane, whereby the objective compound (6.7 g of primary crystal, 2.5 g of secondary crystal, 9.2 g in total, 90%) was obtained as a white solid.

後処理

  1. customat room temperature
  2. stirringthe solution was stirred for 30 minutes
  3. customthe organic layer was separated
  4. washThe organic layer was washed sequentially with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter the drying agent was removed by filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe resulting residue was crystallized from ethyl acetate-heptane, whereby the objective compound (6.7 g of primary crystal, 2.5 g of secondary crystal, 9.2 g in total, 90%)
  9. customwas obtained as a white solid

出典と根拠

ORDレコード
ord-f842d83c36bd410baa8d50066914b8d3
出典データセット
uspto-grants-2012_11
特許番号
US08314094B2

反応ノート

読み込み中…