Sodium Hydroxide → HCID 67343995, compound

HRID 1910846Notes

Reaction equation

HRID 1910846 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:26]=[CH:25][C:8]([CH2:9][N:10]2[CH:14]=[C:13]([C:15]3[S:16][CH:17]=[C:18]([C:20]([O:22]CC)=[O:21])[N:19]=3)[CH:12]=[N:11]2)=[CH:7][CH:6]=1>O.CCO>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[CH:14]=[C:13]([C:15]3[S:16][CH:17]=[C:18]([C:20]([OH:22])=[O:21])[N:19]=3)[CH:12]=[N:11]2)=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67341813HCID 67341813, compound

Product 1

HCID 67343995HCID 67343995, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

According to Scheme 1 Step 6: A solution of NaOH (38.4 mmol, 12.8 mL) in water (3 M) was added at 0° C. to a solution of ethyl 2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazole-4-carboxylate (15.4 mmol, 5.28 g) in EtOH (38 mL) and the reaction mixture was heated at 50° C. overnight. After evaporation of the solvent, the crude residue was partitioned between a solution of NaOH (1 M) and EtOAc. After extraction, the organic phase was washed with a solution of NaOH (1 M). The aqueous phase was then acidified and the beige precipitate formed was filtered off, washed with water and dried to yield 2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazole-4-carboxylic acid (13.6 mmol, 4.29 g, 88%) as a beige solid.

Workup

  1. customAfter evaporation of the solvent
  2. customthe crude residue was partitioned between a solution of NaOH (1 M) and EtOAc
  3. extractionAfter extraction
  4. washthe organic phase was washed with a solution of NaOH (1 M)
  5. customthe beige precipitate formed
  6. filtrationwas filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-f48a7f8391f440a49f2004ec2bc6f632
Source dataset
uspto-grants-2013_12
Patent number
US08604033B2

Reaction notes

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