Potassium Carbonate → 3,4-Dimethyl-7-(2-methyl-1,3,4-thiadiazol-5-yl)-methoxycoumarin

HRID 483814Notes

Reaction equation

HRID 483814 reaction equation
O[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])=[C:7]([CH3:13])[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.Cl[CH2:16][C:17]1[S:18][C:19](C)=[N:20][N:21]=1.[C:23]([O-])([O-])=[O:24].[K+].[K+]>CC(C)=O>[CH3:13][C:7]1[C:8](=[O:12])[O:9][C:10]2[C:5]([C:6]=1[CH3:14])=[C:4]([O:24][CH3:23])[CH:3]=[C:2]([C:19]1[S:18][C:17]([CH3:16])=[N:21][N:20]=1)[CH:11]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 54129907-hydroxy-3,4-dimethyl-2H-chromen-2-oneHCID 155820072-(Chloromethyl)-5-methyl-1,3,4-thiadiazole

Product 1

HCID 197514973,4-Dimethyl-7-(2-methyl-1,3,4-thiadiazol-5-yl)-methoxycoumarin

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5.0 g of 7-hydroxy-3,4-dimethylcoumarin, 3.9 g of 2-chloromethyl-5-methyl-1,3,4-thiadiazole, 3.5 g of K2CO3 and 100 ml of acetone was refluxed for 20 hours and evaporated down, and the residue was partitioned in H2O/methylene chloride. After the undissolved constituents had been separated off, the organic phase was washed once with 1 N NaOH and then with H2O, dried over Na2SO4 and evaporated down, and the residue was recrystallized from methanol and dried.

Workup

  1. temperaturewas refluxed for 20 hours
  2. customevaporated down
  3. customthe residue was partitioned in H2O/methylene chloride
  4. customAfter the undissolved constituents had been separated off
  5. washthe organic phase was washed once with 1 N NaOH
  6. dry with materialwith H2O, dried over Na2SO4
  7. customevaporated down
  8. customthe residue was recrystallized from methanol
  9. customdried

Sources & evidence

ORD record
ord-5ab5e7b7ac174bcea2d68ce47b9005b7
Source dataset
uspto-grants-1993_07
Patent number
US05227392

Reaction notes

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