Hydrochloric Acid → HCID 57486101, compound

HRID 644444Notes

Reaction equation

HRID 644444 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][C:5]1[S:9][C:8]([NH:10][C:11](=[O:20])[C:12]2[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:13]=2[OH:19])=[N:7][C:6]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+].Cl>CO>[Br:18][C:16]1[CH:15]=[CH:14][C:13]([OH:19])=[C:12]([CH:17]=1)[C:11]([NH:10][C:8]1[S:9][C:5]([CH2:4][C:3]([OH:27])=[O:2])=[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:7]=1)=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86595540HCID 86595540, compound

Product 1

HCID 57486101HCID 57486101, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

{2-[(5-Bromo-2-hydroxybenzoyl)amino]-4-phenylthiazol-5-yl}acetic acid methyl ester (75 mg, 0.17 mmol) was dissolved in methanol (5 mL). 2N Sodium hydroxide (0.5 mL, 1 mmol) was added, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate. After the ethyl acetate layer was washed successively with water and brine, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was suspended and washed with n-hexane-ethyl acetate under heating at reflux to give the title compound (56 mg, 77.3%) as a light yellow white crystal.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the ethyl acetate layer was washed successively with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washwashed with n-hexane-ethyl acetate
  6. temperatureunder heating
  7. temperatureat reflux

Sources & evidence

ORD record
ord-75211ff5db4f45feb33f2f067f719c96
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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