Phenyl thioxochloroformate → HCID 11507578, compound

HRID 1924874Notes

Reaction equation

HRID 1924874 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)[N:3]=[CH:2]1.C([O-])(O)=O.[Na+].C1C=CC(OC(Cl)=[S:34])=CC=1>C1COCC1.O>[S:34]=[C:2]1[NH:3][C:4]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)=[CH:5][NH:1]1

Participants

6

Reactant 3

HCID 70498Phenyl thioxochloroformateHCID 516892Sodium BicarbonateHCID 178509560HCID 178509560, compound2×

Product 1

HCID 11507578HCID 11507578, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2′-(1H-imidazol-4-ylmethyl)-biphenyl-4-carbonitrile (Intermediate D3) (0.36 g, 1.4 mmol) in THF (11 mL) and water (10 mL) was treated with NaHCO3 (1.2 g) at rt for 5 m. Phenyl chlorothionoformate (0.95 mL, 7.0 mmol) was added and stirring was continued for 16 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 (15 mL) and treated with NEt3 (2.0 mL) for 18 h. The solvent was removed under vacuum and the product was washed on a glass frit with CH2Cl2 and pentane to give a solid 2′-(2-thioxo-2,3-dihydro-1H-imidazol-4-ylmethyl)-biphenyl-4-carbonitrile (Compound 6) in 40% yield. 1H NMR (300 MHz, DMSO-d6): δ 11.8 (s, 1H), 11.6 (s, 1H), 7.92 (d, J=9 Hz, 2H), 7.52 (d, J=9 Hz, 2H), 7.44-7.19 (m, 4H), 6.14 (s, 1H), 3.63 (s, 2H).

Workup

  1. extractionextracted with ether (4×15 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. dissolutionThe residue was dissolved in MeOH (15 mL)
  5. additiontreated with NEt3 (2.0 mL) for 18 h
  6. customThe solvent was removed under vacuum
  7. washthe product was washed on a glass frit with CH2Cl2 and pentane

Sources & evidence

ORD record
ord-7017bf262b944a74833eff8d94b2470c
Source dataset
uspto-grants-2012_05
Patent number
US08178571B2

Reaction notes

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