Hydrochloric Acid → HCID 178431884, compound

HRID 1290233Notes

Reaction equation

HRID 1290233 reaction equation
[CH3:1][C:2]1[C:3]([CH:7]([C:9]2[N:10]=[CH:11][N:12](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:13]=2)O)=[CH:4][S:5][CH:6]=1.Cl.[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38]>CCO.[OH-].[OH-].[Pd+2]>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38].[CH3:1][C:2]1[C:3]([CH2:7][C:9]2[N:10]=[CH:11][NH:12][CH:13]=2)=[CH:4][S:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 444972Fumaric AcidHCID 10717796HCID 10717796, compound

Product 1

HCID 178431884HCID 178431884, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of (4-methylthien-3-yl)-1-trityl-imidazol-4-yl-methanol (2.5 g, 5.7 mmol) was combined with 1N HCl (6 mL) and Pd(OH)2 (1.25 g) in EtOH and hydrogenated (55 psi) at 50° C. for 48 hrs. The catalyst was removed by filtration through Dicalite, and the solvent was evaporated in vacuo. The residue was dissolved in water, washed twice with Et2 O, and then basified with Na2CO3 and extracted twice with EtOAc. The combined extracts were dried (K2CO3), filtered, and the solvent was evaporated. The residue was dissolved in 2-PrOH and combined with fumaric acid (0.57 g, 1 eq.). After standing overnight a white solid was collected and recrystallized from acetone to give the title compound m.p. 142°-144° C. 1H NMR (DMSO-d6) supported the assigned structure: δ2.15 (s, 3H), 3.75 (s, 2H), 6.6 (s, 2H), 6.75 (s, 1H), 7.05 (m, 1H), 7.15 (m, 1H), 7.65 (s, 1H). Elemental analysis: Calc. for C9H10N2S.C4H4O4C, 53.05; H, 4.79; N, 9.52. Found C, 53.03; H, 4.73; N, 9.38.

Workup

  1. customThe catalyst was removed by filtration through Dicalite
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. washwashed twice with Et2 O
  5. extractionextracted twice with EtOAc
  6. dry with materialThe combined extracts were dried (K2CO3)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. dissolutionThe residue was dissolved in 2-PrOH
  10. customa white solid was collected
  11. customrecrystallized from acetone

Sources & evidence

ORD record
ord-f6975f7ed19c4db4b6420ace61cd9428
Source dataset
uspto-grants-1998_05
Patent number
US05750720

Reaction notes

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