Chromocarb → HCID 70169091, compound

HRID 2230075Notes

Reaction equation

HRID 2230075 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[C:2]1[C:12](O)=[O:13].S(Cl)(Cl)=O.[CH3:19][C:20]1[N:24]([CH2:25][CH2:26][OH:27])[C:23]([N+:28]([O-:30])=[O:29])=[CH:22][N:21]=1>>[CH3:19][C:20]1[NH:24][C:23]([N+:28]([O-:30])=[O:29])=[CH:22][N:21]=1.[O:11]=[C:4]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[O:1][C:2]([C:12]([O:27][CH2:26][CH3:25])=[O:13])=[CH:3]1

Participants

4

Reactant 3

HCID 2741ChromocarbHCID 4173MetronidazoleHCID 24386Thionyl Chloride

Product 1

HCID 70169091HCID 70169091, compoundYield 31.1%

Procedure

The reaction mixture of chromone-2-carboxylic acid (190 mg, 1.0 mmol) and thionyl chloride (2 ml) was refluxed for 2 h. The excessive thionyl chloride was evaporated under vacuum. The residue was dissolved in 5 ml of dichloromethane. To this solution, metronidazole (162 mg, 0.95 mmol) was added. After the mixture was stirred at room temperature overnight some solid came out. The solid was filtered and was recrystallized from C2H5OH-CH3OH to give 102 mg 2-methyl-5-nitro-1H-imidazole-1-ethyl 4-oxo-4H-1-benzopyran-2-carboxylate. m.p.: 210-212° (dec.).

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe excessive thionyl chloride was evaporated under vacuum
  3. dissolutionThe residue was dissolved in 5 ml of dichloromethane
  4. filtrationThe solid was filtered
  5. customwas recrystallized from C2H5OH-CH3OH

Sources & evidence

ORD record
ord-8aae9776a3324df8bffa1e331b24b788
Source dataset
uspto-grants-2002_07
Patent number
US06423707B1

Reaction notes

Loading…