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

HRID 1584499Notes

Reaction equation

HRID 1584499 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 516892Sodium BicarbonateSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-12cbb352fcf24ecf9f696539681bc660
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

Loading…