Water → (S)-N-methyl-N-(2-phenylpent-4-enyl)-2-methoxy-5-(4H-triazol-4-yl)benzamide

HRID 429494ノート

反応式

HRID 429494 の反応式
[CH3:1][NH:2][CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:5][CH:6]=[CH2:7].O.[CH3:15][O:16][C:17]1[CH:25]=[CH:24][C:23]([CH:26]2[CH:30]=[N:29][N:28]=[N:27]2)=[CH:22][C:18]=1[C:19](Cl)=[O:20].CO.ClCCl>CC(C)=O.C(=O)(O)[O-].[Na+]>[CH3:1][N:2]([CH2:3][CH:4]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:5][CH:6]=[CH2:7])[C:19](=[O:20])[C:18]1[CH:22]=[C:23]([C@H:26]2[CH:30]=[N:29][N:28]=[N:27]2)[CH:24]=[CH:25][C:17]=1[O:16][CH3:15]

参加物

7

反応物 4

HCID 962WaterHCID 18354441N-methyl-(2-phenylpent-4-enyl)amineHCID 183544512-methoxy-5-(4H-triazol-4-yl)benzoyl chlorideHCID 21226129Dichloromethane methanol

生成物 1

HCID 69775799(S)-N-methyl-N-(2-phenylpent-4-enyl)-2-methoxy-5-(4H-triazol-4-yl)benzamide

試薬・触媒・溶媒 2

HCID 180Acetone溶媒2 回HCID 516892Sodium Bicarbonate溶媒2 回

実験手順

Combine N-methyl-(2-phenylpent-4-enyl)amine (1.00 g, 5.7 mmol), acetone (50 mL), water (20 mL), and sodium bicarbonate (0.3 g, 2.85 mmol). Add portionwise, a solution of 2-methoxy-5-(4H-triazol-4-yl)benzoyl chloride (1.4 g, 6.3 mmol) in acetone (50 mL). After 10 hours, dilute the reaction mixture with a saturated aqueous sodium bicarbonate solution and evaporate in vacuo to remove most of the acetone. Extract five times with dichloromethane. Dry the combined organic layers over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 5% methanol/dichloromethane to give (S)-N-methyl-N-(2-phenylpent-4-enyl)-2-methoxy-5-(4H-triazol-4-yl)benzamide: Rf=0.25 (silica gel, 5% methanol/dichloromethane).

後処理

  1. additionAdd portionwise
  2. customevaporate in vacuo
  3. customto remove most of the acetone
  4. extractionExtract five times with dichloromethane
  5. dry with materialDry the combined organic layers over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customto give a residue

出典と根拠

ORDレコード
ord-44c6264170524737991b7d860f206cd1
出典データセット
uspto-grants-2001_11
特許番号
US06316445B1

反応ノート

読み込み中…