Lithium Hydroxide → HCID 67467360, compound

HRID 1406268Notes

Reaction equation

HRID 1406268 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([F:14])[CH:8]=[C:9]2[S:13][CH:12]=[N:11][C:10]=12)=[O:4].[OH-].[Li+]>O1CCCC1>[F:14][C:7]1[CH:8]=[C:9]2[S:13][CH:12]=[N:11][C:10]2=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 53413095Methyl 6-fluoro-4-benzothiazolecarboxylate

Product 1

HCID 67467360HCID 67467360, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-fluoro-benzothiazole-4-carboxylic acid methyl ester (1.97 g, 9.33 mmol) in tetrahydrofuran (30 mL) was added aqueous lithium hydroxide solution (2M, 14.0 mL, 28 mmol, 3 eq.) and then stirred, at room temperature, for 4 hr. The reaction mixture was quenched with aqueous hydrochloric acid (2M, 30 mL) and stirred for 15 min. The resulting suspension was filtered and the solid produced was washed with water and air dried to give the title compound as a grey solid (1.51 g, 82%).

Workup

  1. customThe reaction mixture was quenched with aqueous hydrochloric acid (2M, 30 mL)
  2. stirringstirred for 15 min
  3. filtrationThe resulting suspension was filtered
  4. customthe solid produced
  5. washwas washed with water and air
  6. customdried

Sources & evidence

ORD record
ord-4bf6b7af6c3740719a1f51777b9d8357
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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