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

HRID 401623Notes

Reaction equation

HRID 401623 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 1y (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 1z (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-0c227b96794c4eb9b4eac9a3aa427879
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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