Dimethylformamide → HCID 19751464, compound

HRID 483813Notes

Reaction equation

HRID 483813 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.[H-].[Na+].Cl[CH2:18][C:19]1[O:20][C:21](C)=[N:22][N:23]=1.CN(C)[CH:27]=[O:28]>>[CH3:13][C:7]1[C:8](=[O:12])[O:9][C:10]2[C:5]([C:6]=1[CH3:14])=[C:4]([O:28][CH3:27])[CH:3]=[C:2]([C:21]1[O:20][C:19]([CH3:18])=[N:23][N:22]=1)[CH:11]=2

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 38266202-(Chloromethyl)-5-methyl-1,3,4-oxadiazoleHCID 54129903,4-Dimethylumbelliferone

Product 1

HCID 19751464HCID 19751464, compound

Procedure

5.0 g of 7-hydroxy-3,4-dimethylcoumarin in 20 ml of diemthylformamide were added dropwise to a suspension 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. additionwere added
  2. filtrationthe precipitated solid was filtered off under suction
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-3859d89f673d45c88b8de2624f16c906
Source dataset
uspto-grants-1993_07
Patent number
US05227392

Reaction notes

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