2-Mercaptoethanol → 1-[2-Naphthoylmethyl]imidazole ethylene

HRID 26543

Reaction equation

HRID 26543 reaction equation
Cl.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)=[O:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.SCCO.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC=CC=1>[CH2:2]=[CH2:3].[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)=[O:13]

Participants

7

Reactant 4

HCID 15672-MercaptoethanolHCID 11430Potassium CarbonateHCID 51199Nafimidone monohydrochlorideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 213237211-[2-Naphthoylmethyl]imidazole ethylene

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent2×

Procedure

1-[2-Naphthoylmethyl]imidazole hydrochloride (540 mg) and p-toluenesulfonic acid monohydrate (570 mg) in toluene (10 ml) containing a little benzene are treated with 2-mercaptoethanol (4 ml). A pressure-equalized addition funnel filled with activated 4 A molecular sieves in toluene is placed above the flask as a modified Dean-Stark trap and the mixture heated under reflux with stirring for 18 hours. The resulting mixture is then added with stirring to excess aqueous potassium carbonate, the product extracted with ether (with filtration) and the extracts washed, dried (MgSO4) and evaporated. Purification by chromatography on silica gel eluting with ethyl acetate gives pure 1-[2-naphthoylmethyl]imidazole ethylene hemithioketal.

Workup

  1. additionA pressure-equalized addition funnel filled
  2. temperaturethe mixture heated
  3. temperatureunder reflux
  4. additionThe resulting mixture is then added
  5. extractionthe product extracted with ether (with filtration)
  6. washthe extracts washed
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customPurification by chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-6f6446b2cdd849b38d161af93dc6bd9e
Source dataset
uspto-grants-1979_04
Patent number
US04150153

Linked notes

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