Lithium hydroxide, monohydrate → HCID 54100039, compound

HRID 2186232Notes

Reaction equation

HRID 2186232 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:15]([O:17]C)=[O:16])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[N:6]=1.O.[OH-].[Li+]>CO.O>[Br:1][C:2]1[S:3][C:4]([C:15]([OH:17])=[O:16])=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=2)[N:6]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 54495312HCID 54495312, compound

Product 1

HCID 54100039HCID 54100039, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-bromo-4-[(4-methoxy)phenyl]-5-(methoxycarbonyl)thiazole (6.24 g, 19.74 mmol) in 20 mL of methanol and 20 mL of water was added lithium hydroxide monohydrate (0.91 g, 21.7 mmol). The mixture was stirred at ambient temperature for 1 h, whereupon aditional lithium hydroxide monohydrate (0.91 g, 21.7 mmol) was added. After stirring an additional hour, the volatiles were removed in vacuo and the residue was quenched with 10% aq HCl. The mixture was extracted with ethyl acetate and the organics were washed with brine, dried (MgSO4) and concentrated. The residue was recrystallized from chloroform/hexane to afford 2.2 g (37%) of the title compound as a white solid. LRMS (ES−): 303 (M−H)−.

Workup

  1. additionwas added
  2. customthe volatiles were removed in vacuo
  3. customthe residue was quenched with 10% aq HCl
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was recrystallized from chloroform/hexane

Sources & evidence

ORD record
ord-7adf0c1c59a94c419b0803949af85ea0
Source dataset
uspto-grants-2002_06
Patent number
US06403620B1

Reaction notes

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