2-Mercaptoethanol → HCID 20475869, compound

HRID 905207Notes

Reaction equation

HRID 905207 reaction equation
Cl.[CH2:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:14]([CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)=[O:15])[CH:8]=[CH:7]2)[CH3:3].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].[CH2:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:14]([CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)=[O:15])[CH:8]=[CH:7]2)[CH3:3]

Participants

7

Reactant 4

HCID 15672-MercaptoethanolHCID 11430Potassium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 20475916HCID 20475916, compound

Product 1

HCID 20475869HCID 20475869, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent2×

Procedure

1-[(6-Ethyl-2-naphthoyl)methyl]imidazole hydrochloride (600 mg.) and p-toluenesulfonic acid monohydrate (570 mg.) in toluene (100 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-[(6-ethyl-2-naphthoyl)methyl]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-439c05f6a37943a88fa2aff1064d5e90
Source dataset
uspto-grants-1983_12
Patent number
US04423057

Reaction notes

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