Triethylamine → HCID 14673929, compound

HRID 1199418Notes

Reaction equation

HRID 1199418 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:30])[C:26]([CH3:29])([CH3:28])[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:30])[C:26]([CH3:29])([CH3:28])[CH3:27])[CH:3]1[OH:16])=[N:10][O:11][N:12]=3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl 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 14673929HCID 14673929, compoundYield 70%

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 μl (0.935 m mol) of triethylamine and 20 ml of methylene chloride were added 115 μl (0.935 m mol) of pivaloyl chloride (trimethylacetyl chloride) with stirring at the room temperature, followed by further stirring for 3.5 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 the pure intended compound. (yield: 191 mg, yield: 70%).

Workup

  1. stirringby further stirring for 3.5 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
  7. customto obtain the pure intended compound

Sources & evidence

ORD record
ord-aa6c8f27c0fd4d1db092e334b567ebad
Source dataset
uspto-grants-1990_02
Patent number
US04900752

Reaction notes

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