p-Chlorothiophenol → HCID 66986382, compound

HRID 1254032Notes

Reaction equation

HRID 1254032 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.I[C:12]1[N:13]=[C:14]([CH3:27])[NH:15][C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1>CN1C(=O)CCC1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:12]2[N:13]=[C:14]([CH3:27])[NH:15][C:16]=2[C:17]2[CH:18]=[CH:19][C:20]([S:23]([CH3:26])(=[O:24])=[O:25])=[CH:21][CH:22]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 24758Sodium hydrideHCID 178433059HCID 178433059, compound

Product 1

HCID 66986382HCID 66986382, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To NaH (60% in mineral oil, 0.12 g, 3.0 mmol) in NMP (10 mL) was added 4-chlorobenzenethiol (0.44 g, 3.0 mmol). After stirring for 15 min, the reaction mixture was added to the product of Step 3 (1.09 g, 3.0 mmol) and CuBr (0.65 g, 4.5 mmol) in NMP (10 mL) under argon. The resulting mixture was kept at 140° C. for 4 h. After cooling, the reaction mixture was partitioned between H2O and EtOAc. The organic layer was separated, filtered through a thin pad of silica gel, and the filtrate was dried over anhydrous Na2SO4, and concentrated. The residue was purified by chromatography on silica gel (DCM to EtOAc) to give 4-[(4-chlorophenyl)thio]-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-imidazole. LCMS: [M+1]+=379.0

Workup

  1. waitThe resulting mixture was kept at 140° C. for 4 h
  2. temperatureAfter cooling
  3. customthe reaction mixture was partitioned between H2O and EtOAc
  4. customThe organic layer was separated
  5. filtrationfiltered through a thin pad of silica gel
  6. dry with materialthe filtrate was dried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (DCM to EtOAc)

Sources & evidence

ORD record
ord-c0aeac63912c4538a55a6fd36839c596
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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