Ethyl Acetate → HCID 18182198, compound

HRID 1359424Notes

Reaction equation

HRID 1359424 reaction equation
[CH2:1]([C:8]1[N:9]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]3[O:19][CH2:20][O:21][C:15]=3[CH:14]=2)[S:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.[Br:28]N1C(=O)CCC1=O>CN(C)C=O>[CH2:1]([C:8]1[N:9]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]3[O:19][CH2:20][O:21][C:15]=3[CH:14]=2)[S:11][C:12]=1[Br:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 18182359HCID 18182359, compound

Product 1

HCID 18182198HCID 18182198, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

367 mg of 4-benzyl-2-(3,4-methylenedioxyphenyl)thiazole was dissolved in 2 ml of N,N-dimethylformamide 244 mg of N-bromosuccinimide was added thereto under ice-cooling, followed by stirring overnight. Then, ethyl acetate was added to the reaction solution, followed by washing with water. The organic phase was further washed with brine, dried over anhydrous sodium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 3% ethyl acetate/hexane as an eluent for separation and purification, to give 377 mg of the target compound.

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. washby washing with water
  4. washThe organic phase was further washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed
  7. customfor separation and purification

Sources & evidence

ORD record
ord-0bda1a47ac0d4c2b90e402f4315e03f1
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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