Hydrochloric Acid → HCID 23043789, compound

HRID 2165118Notes

Reaction equation

HRID 2165118 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1/[CH:7]=[C:8]1/[C:9](=[O:21])[C:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:12][C:11]=2[CH2:19][CH2:20]/1.[ClH:22].C(O)C>[Pd].ClCCl.CO>[ClH:22].[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][CH:8]1[CH2:20][CH2:19][C:11]2[S:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:10]=2[C:9]1=[O:21]

Participants

7

Reactant 3

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 23043782HCID 23043782, compound

Product 1

HCID 23043789HCID 23043789, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (E)-3,4-dihydro-2-[(5-methyl-1H-imidazol-4-yl) methylene]-1(2H)-dibenzothiophenone (599 mg), 2N hydrochloric acid (2 ml) and ethanol (50 ml) was hydrogenated at atmospheric pressure and room temperature using a 10% palladium on charcoal catalyst (60 mg) for 20 h. The suspension was warmed on a steam bath for 10 min and then filtered. The filtrate was evaporated to give an oil which was purified by FCC eluting with System A (100:10:1) to give a solid. A solution of this solid in a mixture of dichloromethane (20 ml) and methanol (5 ml) was treated with a slight excess of ethereal hydrogen chloride. The solution was evaporated to give the title compound (449 mg), m.p. 266°-269°, t.l.c. (System A 100:10:1) Rf 0.3.

Workup

  1. customwas hydrogenated at atmospheric pressure and room temperature
  2. customfor 20 h
  3. temperatureThe suspension was warmed on a steam bath for 10 min
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customto give an oil which
  7. customwas purified by FCC
  8. washeluting with System A (100:10:1)
  9. customto give a solid
  10. customThe solution was evaporated

Sources & evidence

ORD record
ord-f9e30bf8fae5445bb7fa5d0e9346dd69
Source dataset
uspto-grants-1990_07
Patent number
US04939144

Reaction notes

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