Hydrochloric Acid → 5-Bromo-N-{4-[(1,1-dimethyl)ethyl]thiazol-2-yl)-2-hydroxybenzamide

HRID 2384463Notes

Reaction equation

HRID 2384463 reaction equation
C([O:4][C:5]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:6]=1[C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[N:14]=1)=[O:8])(=O)C.[OH-].[Na+].Cl>O1CCCC1>[Br:23][C:20]1[CH:21]=[CH:22][C:5]([OH:4])=[C:6]([CH:19]=1)[C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([C:15]([CH3:16])([CH3:17])[CH3:18])[N:14]=1)=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 85823490Acetoxy-5-bromo-N-{4-[(1,1-dimethyl)ethyl]thiazol-2-yl}benzamide

Product 1

HCID 103161555-Bromo-N-{4-[(1,1-dimethyl)ethyl]thiazol-2-yl)-2-hydroxybenzamideYield 78.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Acetoxy-5-bromo-N-{4-[(1,1-dimethyl)ethyl]thiazol-2-yl}benzamide (100.1 mg, 0.25 mmol) was dissolved in tetrahydrofuran (3 mL). 2 N sodium hydroxide (0.2 ml) was added, and the mixture was stirred at room temperature for 20 minutes. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation under reduced pressure was crystallized (isopropyl ether/n-hexane) to give the title compound (70.1 mg, 78.9%) as a light gray solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe residue obtained by evaporation under reduced pressure
  5. customwas crystallized (isopropyl ether/n-hexane)

Sources & evidence

ORD record
ord-7d534732382e45f5b50bd25b5563abea
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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