Sodium Hydroxide → HCID 70982355, compound

HRID 1409375Notes

Reaction equation

HRID 1409375 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([C:25]2[CH:29]=[C:28]([C:30]([O:32]CC)=[O:31])[NH:27][N:26]=2)[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[C:1]([N:20]1[CH:24]=[C:23]([C:25]2[CH:29]=[C:28]([C:30]([OH:32])=[O:31])[NH:27][N:26]=2)[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70982312HCID 70982312, compound

Product 1

HCID 70982355HCID 70982355, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 3-(1-trityl-1H-imidazol-4-yl)-1H-pyrazole-5-carboxylate (4.01 mmol, 1.8 g) was dissolved in ethanol (20 ml) and cooled to 0° C. NaOH 2 M solution (8.03 mmol, 4.01 ml) was added and the mixture was stirred at RT for an hour. The mixture was heated to 60° C. and stirred for 10 h. Ethanol was evaporated and the residue was diluted with water. The pH was adjusted to 4 with 1 M HCl solution which precipitated the product. The precipitate was removed by filtration and washed with water. The solid was dried under vacuum. 1.5 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 6.75 (bs, 1H), 7.08-7.17 (m, 6H), 7.18-7.34 (m, 5H), 7.36-7.49 (m, 8H). LC-MS: [M−1]=419.1.

Workup

  1. temperatureThe mixture was heated to 60° C.
  2. stirringstirred for 10 h
  3. customEthanol was evaporated
  4. additionthe residue was diluted with water
  5. customprecipitated the product
  6. customThe precipitate was removed by filtration
  7. washwashed with water
  8. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-50babde092f64428b95d84f5a11efbae
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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