Acetyl chloride → HCID 14673922, compound

HRID 1199416Notes

Reaction equation

HRID 1199416 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:27])[CH3:26]>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:27])[CH3:26])[CH:3]1[OH:16])=[N:10][O:11][N:12]=3

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 11107308(+)-7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole

Product 1

HCID 14673922HCID 14673922, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 200 mg (0.850 m mol) of 7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano [2,3-f] benzo-2,1,3-oxadiazole, 128 μl (0.917 m mol) of triethylamine and 17 ml of methylene chloride were added 128 μl (0.917 m mol) of acetyl chloride with stirring at 0° C., followed by stirring for 30 minutes. After the completion of the reaction, the precipitated crystals were filtered. The crystals were washed successively with methylene chloride and water and dried at 80° C. under reduced pressure to obtain 223 mg (yield: 88%) of the intended compound.

Workup

  1. stirringby stirring for 30 minutes
  2. customAfter the completion of the reaction
  3. filtrationthe precipitated crystals were filtered
  4. washThe crystals were washed successively with methylene chloride and water
  5. customdried at 80° C. under reduced pressure

Sources & evidence

ORD record
ord-1191c7eb850d4c0e8f5081cd6530074b
Source dataset
uspto-grants-1990_02
Patent number
US04900752

Reaction notes

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