Phenyl thioxochloroformate → HCID 11637318, compound

HRID 1924871Notes

Reaction equation

HRID 1924871 reaction equation
C(O)(=O)/C=C/C(O)=O.[Cl:9][C:10]1[C:11]([F:22])=[C:12]([CH:19]=[CH:20][CH:21]=1)[CH2:13][C:14]1[NH:18][CH:17]=[N:16][CH:15]=1.C([O-])(O)=O.[Na+].C1C=CC(OC(Cl)=[S:36])=CC=1>C1COCC1.O>[Cl:9][C:10]1[C:11]([F:22])=[C:12]([CH:19]=[CH:20][CH:21]=1)[CH2:13][C:14]1[NH:18][C:17](=[S:36])[NH:16][CH:15]=1

Participants

6

Reactant 3

HCID 70498Phenyl thioxochloroformateHCID 516892Sodium BicarbonateHCID 131728323HCID 131728323, compound2×

Product 1

HCID 11637318HCID 11637318, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(3-chloro-2-fluoro-benzyl)-1H-imidazole fumaric acid salt (Intermediate B3) (0.24 mmol) in THF (3 mL) and water (3 mL) was treated with NaHCO3 (0.12 g) at rt for 10 m. Phenyl chlorothionoformate (0.11 mL, 0.6 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 (5 mL) and treated with NEt3 (0.3 mL) for 16 h. The solvent was removed under vacuum and the product was washed on a glass frit with CH2Cl2 to give a white solid, 4-(3-chloro-2-fluoro-benzyl)-1,3-dihydro-imidazole-2-thione (Compound 2).

Workup

  1. extractionextracted with ether (3×15 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. dissolutionThe residue was dissolved in MeOH (5 mL)
  5. additiontreated with NEt3 (0.3 mL) for 16 h
  6. customThe solvent was removed under vacuum
  7. washthe product was washed on a glass frit with CH2Cl2

Sources & evidence

ORD record
ord-b3860551adc147e4b5dbfab1012254ca
Source dataset
uspto-grants-2012_05
Patent number
US08178571B2

Reaction notes

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