Methyl iodide → 1-Methyl-5-(2,3-epoxypropoxy)-8-benzyloxy-3,4-dihydrocarbostyril

HRID 1155573Notes

Reaction equation

HRID 1155573 reaction equation
[O:1]1[CH2:24][CH:2]1[CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:23])[NH:10]2.[H-].[Na+].[CH3:27]I.[Cl-].[NH4+]>CS(C)=O>[CH3:27][N:10]1[C:11]2[C:6](=[C:5]([O:4][CH2:3][CH:2]3[O:1][CH2:24]3)[CH:14]=[CH:13][C:12]=2[O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:7][CH2:8][C:9]1=[O:23]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 12751742HCID 12751742, compound

Product 1

HCID 127518381-Methyl-5-(2,3-epoxypropoxy)-8-benzyloxy-3,4-dihydrocarbostyrilYield 49.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

3.3 g of 5-(2,3-epoxypropoxy)-8-benzyloxy-3,4-dihydrocarbostyril was dissolved in 50 ml of dimethyl sulfoxide, and 1.3 g of 50% sodium hydride was added to the solution followed by stirring at room temperature for 30 minutes. 2.9 g of methyl iodide dissolved in 10 ml of dimethyl sulfoxide was added dropwise thereto, and the resulting mixture was stirred at room temperature for 2 hours. 200 ml of a saturated aqueous solution of ammonium chloride was added to the reaction mixture followed by extracting with chloroform. The chloroform layer was washed with water and then dried over anhydrous sodium sulfate. The chloroform was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography and recrystallized from ethanol to obtain 1.7 g of 1-methyl-5-(2,3-epoxypropoxy)-8-benzyloxy-3,4-dihydrocarbostyril as yellow needle-like crystals having a melting point of 111°-112.5° C.

Workup

  1. additionwas added dropwise
  2. stirringthe resulting mixture was stirred at room temperature for 2 hours
  3. extractionby extracting with chloroform
  4. washThe chloroform layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe chloroform was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-cf2e6bc8892a49ef83a76462657ca165
Source dataset
uspto-grants-1981_11
Patent number
US04302588

Reaction notes

Loading…