Phenyl thioxochloroformate → HCID 11687529, compound

HRID 1924870Notes

Reaction equation

HRID 1924870 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:3]=1[CH2:4][C:5]1[NH:9][CH:8]=[N:7][CH:6]=1.C([O-])(O)=O.[Na+].C1C=CC(OC(Cl)=[S:28])=CC=1>C1COCC1.O>[Cl:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:2]([Cl:1])[C:3]=1[CH2:4][C:5]1[NH:9][C:8](=[S:28])[NH:7][CH:6]=1

Participants

6

Reactant 3

HCID 70498Phenyl thioxochloroformateHCID 516892Sodium BicarbonateHCID 3061239HCID 3061239, compound2×

Product 1

HCID 11687529HCID 11687529, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(2,6-dichloro-benzyl)-1H-imidazole (Intermediate A4) (0.34 g, 1.5 mmol) in THF (6 mL) and water (6 mL) was treated with NaHCO3 (1.2 g) at rt for 10 m. Phenyl chlorothionoformate (0.60 mL, ˜4.3 mmol) was added and stirring was continued for 3 h. The mixture was diluted with water (10 mL) and extracted with ether (4×15 mL). The organic portions were combined, dried over MgSO4, filtered and freed of solvent. The residue was dissolved in MeOH (6 mL) and treated with NEt3 (0.6 mL) for 18 h. The solvent was removed under vacuum and the product was washed on a glass frit with CH2Cl2 to give a white solid 4-(2,6-dichloro-benzyl)-1,3-dihydro-imidazole-2-thione (Compound 1) in ˜50% yield.

Workup

  1. extractionextracted with ether (4×15 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. dissolutionThe residue was dissolved in MeOH (6 mL)
  5. additiontreated with NEt3 (0.6 mL) for 18 h
  6. customThe solvent was removed under vacuum
  7. washthe product was washed on a glass frit with CH2Cl2

Sources & evidence

ORD record
ord-6a08db9cb93f4d988b25b04ef4a17ecc
Source dataset
uspto-grants-2012_05
Patent number
US08178571B2

Reaction notes

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