Hydrochloric Acid → HCID 18426847, compound

HRID 1281132Notes

Reaction equation

HRID 1281132 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[NH:16][C:17]4[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[CH:20][C:18]=4[N:19]=3)=[CH:11][CH:10]=2)[S:3]1.[Mg].O.Cl>CO>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[NH:19][C:18]4[CH:20]=[C:21]([Cl:25])[C:22]([Cl:24])=[CH:23][C:17]=4[N:16]=3)=[CH:11][CH:10]=2)[S:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5462224MagnesiumHCID 178518440HCID 178518440, compound

Product 1

HCID 18426847HCID 18426847, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2-[4-[(2,4-dioxothiazolidin-5-ylidene)methyl]phenyl]-5,6-dichlorobenzimidazole (100 mg, 0.256 mmol) and magnesium turnings (125 mg, 5.1 mmol) in methanol (20 mL) was stirred for 40 h at room temperature. Water and hydrochloric acid (1 mol/L) was added, and the mixture was extracted with ethyl acetate. The organic layer was washed washed with water and brine, dried on anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (10:1 chloroform/methanol) and triturated with ethanol to give 2-[4-[(2,4-dioxothiazolidin-5-yl)methyl]phenyl]-5,6-dichlorobenzimidazole (20 mg, 20%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed
  3. washwashed with water and brine
  4. dry with materialdried on anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (10:1 chloroform/methanol)
  7. customtriturated with ethanol

Sources & evidence

ORD record
ord-4eb9768f8ff146e4bfd8031f7f18382d
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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