Phenyl thioxochloroformate → HCID 11528775, compound

HRID 747271Notes

Reaction equation

HRID 747271 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]3[N:12]=[CH:13][NH:14][CH:15]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.C([O-])(O)=O.[Na+].C1C=CC(OC(Cl)=[S:29])=CC=1>C1COCC1.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]3[NH:12][C:13](=[S:29])[NH:14][CH:15]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 70498Phenyl thioxochloroformateHCID 516892Sodium BicarbonateHCID 178420881HCID 178420881, compound2×

Product 1

HCID 11528775HCID 11528775, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-benzo[1,3]dioxol-5-ylmethyl-1H-imidazole (Intermediate D4) (0.24 g, 1.18 mmol) in THF (4 mL) and water (4 mL) was treated with NaHCO3 (1 g, 11.9 mmol) at rt for 10 m. Phenyl chlorothionoformate (0.42 mL, 3.1 mmol) was added and stirring was continued for 3 h. The mixture was diluted with water (10 mL) and extracted with ether (3×15 mL). The organic portions were combined, dried over MgSO4, filtered and freed of solvent. The residue was dissolved in MeOH (8 mL) and treated with NEt3 (1 mL) for 16 h. The solvent was removed under vacuum and the product was washed on a glass frit with 50% CH2Cl2:hexanes to give a white solid (˜36%) 4-benzo[1,3]dioxol-5-ylmethyl-1,3-dihydro-imidazole-2-thione (Compound 5)

Workup

  1. extractionextracted with ether (3×15 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. dissolutionThe residue was dissolved in MeOH (8 mL)
  5. additiontreated with NEt3 (1 mL) for 16 h
  6. customThe solvent was removed under vacuum
  7. washthe product was washed on a glass frit with 50% CH2Cl2

Sources & evidence

ORD record
ord-085522ecc4a84cb690d83dcce9219159
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

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