Hydrochloric Acid → 2-Phenyl-1,3-benzothiazole-6-carboxylic acid

HRID 409927Notes

Reaction equation

HRID 409927 reaction equation
[C:1]1([C:7]2[S:8][C:9]3[CH:15]=[C:14]([C:16]([O:18]CC)=[O:17])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-].Cl>C1COCC1.O>[C:1]1([C:7]2[S:8][C:9]3[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 50849803Ethyl 2-phenyl-benzothiazole-6-carboxylate

Product 1

HCID 6204592-Phenyl-1,3-benzothiazole-6-carboxylic acidYield 100.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-phenyl-benzothiazole-6-carboxylate 26b (220 mg, 0.78 mmol) was stirred with LiOH (74 mg, 3.1 mmol) in THF (4 mL) and H2O (4 mL) for 16 h. Aqueous 1N HCl solution was added to the mixture to adjust pH to 3˜4. The resulting mixture was extracted with EtOAc (2×). The organic solution was washed with aq. NaCl, dried over Na2SO4 and concentrated to give 26c (200 mg).

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (2×)
  2. washThe organic solution was washed with aq. NaCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-95d41bf04136431fbf680f868e3dc9f0
Source dataset
uspto-grants-2014_06
Patent number
US08759533B2

Reaction notes

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