Hydrochloric Acid → HCID 57486101, compound

HRID 2384474Notes

Reaction equation

HRID 2384474 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). 2 N 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 2 N hydrochloric acid and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and brine one after another, 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 with water and brine one after another,
  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-8aa8da2c03c544f4b8824093c064c13a
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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