Phenyl thioxochloroformate → 4-[(4-Chloroindol-1-yl)methyl]-1,3-dihydroimidazole-2-thione

HRID 748644Notes

Reaction equation

HRID 748644 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH2:11][C:12]1[NH:13][CH2:14][NH:15][CH:16]=1.C([O-])(O)=O.[Na+].C1C=CC(OC(Cl)=[S:30])=CC=1>C1COCC1.O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH2:11][C:12]1[NH:13][C:14](=[S:30])[NH:15][CH:16]=1

Participants

6

Reactant 3

HCID 70498Phenyl thioxochloroformateHCID 516892Sodium BicarbonateHCID 692039604-(4-Chloro-indol-1-ylmethyl)-1,3-dihydro-imidazole2×

Product 1

HCID 116086344-[(4-Chloroindol-1-yl)methyl]-1,3-dihydroimidazole-2-thioneYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Chloro-indol-1-ylmethyl)-1,3-dihydro-imidazole (Intermediate A4) (0.5 mmol) in THF (3 mL) and water (3 mL) was treated with NaHCO3 (5 mmol) at rt for 20 m. Phenyl chlorothionoformate (1.3 mmol) was added and stirring was continued for 4 h. The mixture was diluted with water (15 mL) and extracted with ether (3×25 mL). The organic portions were combined, dried over MgSO4, filtered and the solvent was removed under vacuum. The residue was dissolved in MeOH (4 mL) and treated with NEt3 (0.35 mL) for 18 h at rt. The solvent was evaporated and the product was washed on a glass frit with 50% CH2Cl2:hexanes to give a solid 4-(4-chloro-indol-1-ylmethyl)-1,3-dihydro-imidazole-2-thione (Compound 1) (˜50%)

Workup

  1. extractionextracted with ether (3×25 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed under vacuum
  5. dissolutionThe residue was dissolved in MeOH (4 mL)
  6. additiontreated with NEt3 (0.35 mL) for 18 h at rt
  7. customThe solvent was evaporated
  8. washthe product was washed on a glass frit with 50% CH2Cl2

Sources & evidence

ORD record
ord-90db86b23eb34d44a2f2e3b1139be000
Source dataset
uspto-grants-2008_07
Patent number
US07399868B2

Reaction notes

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