Triethylamine → HCID 15407875, compound

HRID 2293488Notes

Reaction equation

HRID 2293488 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:4]=[C:3]1[C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1.[Na].[CH2:29](N(CC)CC)C.S(Cl)(Cl)=O>ClCl.CO>[CH3:29][O:24][C:23](=[O:25])[C:22]1[CH:21]=[CH:20][C:19]([C:3]2[N:2]([CH3:1])[C:6]([C:7]3[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=3)=[C:5]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:4]=2)=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 5360545SodiumHCID 10269587HCID 10269587, compound

Product 1

HCID 15407875HCID 15407875, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 24526ChlorineSolvent

Procedure

To a suspension of 4-[1-methyl-4-phenyl-5(4-pyridyl)-imidazol-2-yl]benzoic acid, sodium salt (20 mg, 0.06 mmol) [See Ex. 5 above] in CH2 Cl2 (2 mL.) was added triethylamine (24 mL, 0.17 mmol), followed by thionyl chloride (10 mL, 0.14 mmol). The reaction mixture was stirred at rt for 30 min, at which time MeOH (0.5 mL) was added. The mixture was stirred at rt for an additional 2 h and concentrated under reduced pressure. The residue was purified by flash chromatography, eluting with a solvent gradient of 0-1% MeOH/CHCl3 and recrystallized from EtOAc to afford the title compound as an off-white crystalline solid (1.6 mg, 8%): mp 208°-209° C.

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by flash chromatography
  4. washeluting with a solvent gradient of 0-1% MeOH/CHCl3
  5. customrecrystallized from EtOAc

Sources & evidence

ORD record
ord-def91c00a8194f76a266310667f508da
Source dataset
uspto-grants-1997_11
Patent number
US05686455

Reaction notes

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