Water → N-[2-bromo-4-[4-(3,5-dichlorophenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrole-2-yl]phenylmethyl]phthalimide

HRID 2386158ノート

反応式

HRID 2386158 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([C:8](=O)[CH2:9][C:10]([C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)([CH2:15][N+:16]([O-])=O)[C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:4][C:3]=1[CH2:28][N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39].C([O-])=O.[NH4+].C(OCC)(=O)C.O>O1CCCC1.[Zn]>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[CH2:9][C:10]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)([C:11]([F:13])([F:12])[F:14])[CH2:15][N:16]=2)[CH:5]=[CH:4][C:3]=1[CH2:28][N:29]1[C:30](=[O:39])[C:31]2=[CH:38][CH:37]=[CH:36][CH:35]=[C:32]2[C:33]1=[O:34]

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2723923Ammonium formateHCID 86648070N-[2-bromo-4-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-(nitromethyl) butanoyl]phenylmethyl]phthalimide

生成物 1

HCID 86648071N-[2-bromo-4-[4-(3,5-dichlorophenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrole-2-yl]phenylmethyl]phthalimide

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 0.70 g of N-[2-bromo-4-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-(nitromethyl) butanoyl]phenylmethyl]phthalimide and 1.03 g of ammonium formate in 20 mL of tetrahydrofuran, 1.07 g of zinc powder was added and the resultant reaction mixture was stirred while heating the mixture to reflux for 1 hour. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature, and 100 mL of ethyl acetate and 50 mL of water were added to the reaction mixture, followed by filtering the reaction mixture with Celite. Subsequently, the organic phase was separated off and was dehydrated and dried over a saturated brine and anhydrous magnesium sulfate in this order, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with chloroform to obtain 0.18 g of the objective substance as a white crystal.

後処理

  1. customthe resultant reaction mixture
  2. temperaturewhile heating the mixture
  3. temperatureto reflux for 1 hour
  4. customAfter the completion of the reaction
  5. waitthe reaction mixture was left
  6. filtrationby filtering the reaction mixture with Celite
  7. customSubsequently, the organic phase was separated off
  8. dry with materialdried over a saturated brine and anhydrous magnesium sulfate in this order
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe resultant residue was purified by silica gel column chromatography
  11. washeluting with chloroform
  12. customto obtain 0.18 g of the objective substance as a white crystal

出典と根拠

ORDレコード
ord-fac258c77b014ed6873c6bba1d7f6109
出典データセット
uspto-grants-2012_09
特許番号
US08268754B2

反応ノート

読み込み中…