Dimethylformamide → 3,4-Dimethyl-7-(2-methyl-1,3,4-oxadiazol-5-yl)-methoxycoumarin

HRID 1460984Notes

Reaction equation

HRID 1460984 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[O:18][C:19](C)=[N:20][N:21]=1.CN(C)[CH:25]=[O:26]>[H-].[Na+]>[CH3:13][C:7]1[C:8](=[O:12])[O:9][C:10]2[C:5]([C:6]=1[CH3:14])=[C:4]([O:26][CH3:25])[CH:3]=[C:2]([C:19]1[O:18][C:17]([CH3:16])=[N:21][N:20]=1)[CH:11]=2

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 38266202-(Chloromethyl)-5-methyl-1,3,4-oxadiazoleHCID 54129907-hydroxy-3,4-dimethyl-2H-chromen-2-one

Product 1

HCID 197514643,4-Dimethyl-7-(2-methyl-1,3,4-oxadiazol-5-yl)-methoxycoumarin

Reagents, catalysts & solvents 1

HCID 24758Sodium hydrideSolvent

Procedure

5.0 g of 7-hydroxy-3,4-dimethylcoumarin in 20 ml of 0.9 g of NaH (80%) in 50 ml of dimethylformamide at room temperature. After 45 minutes, 3.5 g of 2-chloromethyl-5-methyl-1,3,4-oxadiazole, dissolved in 20 ml of dimethylformamide, were added and the mixture was stirred overnight at room temperature. The reaction solution was hydrolyzed with ice water, and the precipitated solid was filtered off under suction and recrystallized from methanol.

Workup

  1. customat room temperature
  2. additionwere added
  3. filtrationthe precipitated solid was filtered off under suction
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-576d4fd965194fd09ab516e8d6164556
Source dataset
uspto-grants-1991_12
Patent number
US05073563

Reaction notes

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