Triethylamine → HCID 14673933, compound

HRID 1199419Notes

Reaction equation

HRID 1199419 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:29])[CH:26]([CH3:28])[CH3:27]>ClCCl>[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:29])[CH:26]([CH3:28])[CH3:27])[CH:3]1[OH:16])=[N:10][O:11][N:12]=3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl 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 14673933HCID 14673933, compoundYield 42%

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 triethyl amine and 20 ml of dichloromethane were added 98 μl (0.935 m mol) of isobutyryl chloride with stirring at the room temperature, followed by further stirring for four hours. After the completion of the reaction, the mixture 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 109 mg (yield: 42%) of the pure intended compound.

Workup

  1. stirringby further stirring for four hours
  2. customAfter the completion of the reaction
  3. washthe mixture 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-08a42146a430473784b4acdeb2bbaa36
Source dataset
uspto-grants-1990_02
Patent number
US04900752

Reaction notes

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