3,9-Dimethyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide → HCID 46203574, compound

HRID 602563Notes

Reaction equation

HRID 602563 reaction equation
[I-].[CH3:2][C:3]1[N:10]2[C:6](=[N+:7]([CH3:15])[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[S:5][CH:4]=1.[CH3:16][O-:17].[Na+]>CO>[CH3:15][N:7]1[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10](/[C:3](/[CH3:2])=[CH:4]\[S:5][CH3:6])[C:16]1=[O:17]

Participants

4

Reactant 2

HCID 30775083,9-Dimethyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodideHCID 10942334Sodium Methoxide

Product 1

HCID 46203574HCID 46203574, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

350 mg of 3,9-dimethyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide (1.06 mmol) were solubilized in methanol (60 mL), then 230 mg of NaOMe (4 eq) were added and the solution stirred at room temperature. After 48 h the solvent was evaporated, water was added (25 mL) and the mixture extracted with CH2Cl2 (3×25 mL). The organic layer was dried with MgSO4 and evaporated under reduced pressure. The residue was then purified by flash chromatography on silica gel (eluent: CH2Cl2) to afford 1-methyl-3-[(1Z)-1-(methylsulfanyl)prop-1-en-2-yl]-1,3-dihydro-2H-benzimidazol-2-one as a white powder (200 mg, 80% yield). Under other experimental conditions: 100 mg of iodide (III-R3=R1=Me) (0.30 mmol) were solubilised in methanol (20 mL), then 65 mg of NaOMe (4 eq) were added and the solution refluxed for 2 h. Then, the solvent was evaporated, water was added (15 mL) and the mixture extracted with CH2Cl2 (3×15 mL). 1-methyl-3-[(1Z)-1-(methylsulfanyl)prop-1-en-2-yl]-1,3-dihydro-2H-benzimidazol-2-one was recovered (87%, 62 mg) as the sole (Z) isomer.

Workup

  1. customAfter 48 h the solvent was evaporated
  2. additionwater was added (25 mL)
  3. extractionthe mixture extracted with CH2Cl2 (3×25 mL)
  4. dry with materialThe organic layer was dried with MgSO4
  5. customevaporated under reduced pressure
  6. customThe residue was then purified by flash chromatography on silica gel (eluent: CH2Cl2)

Sources & evidence

ORD record
ord-753985754da84e9fbcca0bbb8691c15a
Source dataset
uspto-grants-2011_03
Patent number
US07906541B2

Reaction notes

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