Phenyl thioxochloroformate → HCID 11694125, compound

HRID 2245389Notes

Reaction equation

HRID 2245389 reaction equation
[C:1]1([CH:7]([C:9]2[NH:13][CH:12]=[N:11][CH:10]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].C1C=CC(OC(Cl)=[S:27])=CC=1>C1COCC1.O>[C:1]1([CH:7]([C:9]2[NH:13][C:12](=[S:27])[NH:11][CH:10]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 70498Phenyl thioxochloroformateHCID 516892Sodium BicarbonateHCID 16663244HCID 16663244, compound2×

Product 1

HCID 11694125HCID 11694125, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(1-phenyl-ethyl)-1H-imidazole (Intermediate C2) (0.20 g, 1.16 mmol) in THF (6 mL) and water (6 mL) was treated with NaHCO3 (0.98 g) at rt for 10 sm. Phenyl chlorothionoformate (0.40 mL, ˜3.0 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 4-(1-phenyl-ethyl)-1,3-dihydro-imidazole-2-thione (Compound 4)

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-b30288992a8149dab7ce59219899d181
Source dataset
uspto-grants-2010_03
Patent number
US07683089B1

Reaction notes

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