Sodium Hydroxide → HCID 67172629, compound

HRID 872934Notes

Reaction equation

HRID 872934 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[CH:17]=[C:16]([C:18]([O:20]CC)=[O:19])[NH:15][N:14]=2)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[CH:17]=[C:16]([C:18]([OH:20])=[O:19])[NH:15][N:14]=2)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 67171392HCID 67171392, compound

Product 1

HCID 67172629HCID 67172629, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 3-(1-benzyl-1H-imidazol-4-yl)-1H-pyrazole-5-carboxylate (0.5 g, 1.687 mmol) was dissolved in methanol (10 ml). The mixture was cooled to 0° C. and sodium hydroxide 2 M solution (1.687 ml) was added. The reaction mixture was allowed to warm to RT with stirring. Stirring was two days during which more sodium hydroxide 2 M solution (3.4 ml in total) was added. The last hour was stirred at 40° C. Methanol was evaporated and water was added. The pH was adjusted to 1 with 1M HCl, which precipitated the product out of the solution. The mixture was filtered, precipitate washed with water and dried with vacuum at 40° C. 1H-NMR (400 MHz; d6-DMSO): δ, 5.82 (s, 2H), 7.17-7.38 (m, 6H), 8.17 (d, 1H), 9.39 (s, 1H), 14.35 (bs, 1H).

Workup

  1. temperatureto warm to RT
  2. stirringStirring
  3. additionwas added
  4. stirringThe last hour was stirred at 40° C
  5. customMethanol was evaporated
  6. additionwater was added
  7. customprecipitated the product out of the solution
  8. filtrationThe mixture was filtered
  9. customprecipitate
  10. washwashed with water
  11. customdried with vacuum at 40° C

Sources & evidence

ORD record
ord-8b5c1ee778fa4785a75dd590d4a4e1b3
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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