Triethylamine → HCID 14673937, compound

HRID 1199421Notes

Reaction equation

HRID 1199421 reaction equation
[CH3:1][C:2]1([CH3:17])[O:14][C:6]2=[CH:7][C:8]3[C:9]([CH:13]=[C:5]2[CH:4]([NH2:15])[CH:3]1[OH:16])=[N:10][O:11][N:12]=3.C(N(CC)CC)C.[C:25](Cl)(=[O:28])[CH2:26][CH3:27]>C(Cl)Cl>[CH3:1][C:2]1([CH3:17])[O:14][C:6]2=[CH:7][C:8]3[C:9]([CH:13]=[C:5]2[CH:4]([NH:15][C:25](=[O:28])[CH2:26][CH3:27])[CH:3]1[OH:16])=[N:10][O:11][N:12]=3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 11107308(+)-7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole

Product 1

HCID 14673937HCID 14673937, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 200 mg (0.85 m mol) of 7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano [2,3-f] benzo-2,1,3-oxadiazole, 130 ml (0.935 m mol) of triethylamine and 20 ml of methylene chloride were added 81 μl (0.935 m mol) of propionyl chloride with stirring at the room temperature, followed by further stirring for 6 hours. After the completion of the reaction, the mixture solution was washed thrice with water and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was recrystallized from ethanol to obtain 77 mg (yield: 31%) of the pure intended compound.

Workup

  1. stirringby further stirring for 6 hours
  2. customAfter the completion of the reaction
  3. washthe mixture solution was washed thrice with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off
  6. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-2ae9e1ba53474164bda4f1fdcfe401cc
Source dataset
uspto-grants-1990_02
Patent number
US04900752

Reaction notes

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