Dimethyl Sulfoxide → HCID 25133789, compound

HRID 424608Notes

Reaction equation

HRID 424608 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH:16]=[N:15][NH:14][C:13](=[O:17])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CS(C)=O.BrN1C(=O)CCC1=O>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[N:15][NH:14][C:13](=[O:17])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 67184N-bromobutanimideHCID 15521373HCID 15521373, compound

Product 1

HCID 25133789HCID 25133789, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(3,4-dimethoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-one (288 mg) was suspended in a mixed solvent of dimethyl sulfoxide (3 ml) and water (0.1 ml), to which N-bromosuccinimide (438 mg) was added under cooling on ice. After the addition was complete, the reaction temperature was raised to room temperature and stirred for 2 hours. The reaction mixture was poured into an ice-cold water and the deposit was filtered. The residue was purified with flash chromatography (SiO2: eluted with ethyl acetate) to obtain the title compound (185 mg, yield 64.7%).

Workup

  1. additionwas added
  2. temperatureunder cooling on ice
  3. additionAfter the addition
  4. filtrationthe deposit was filtered
  5. customThe residue was purified with flash chromatography (SiO2: eluted with ethyl acetate)

Sources & evidence

ORD record
ord-202d7ac9f04c4d5891f4f00590bdc302
Source dataset
uspto-grants-2012_01
Patent number
US08106053B2

Reaction notes

Loading…