Hydrochloric Acid → HCID 59626036, compound

HRID 401632Notes

Reaction equation

HRID 401632 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)C=CC=CC=1.[Li+].[OH-].Cl>C1COCC1.O>[S:8]1[CH:9]=[CH:10][N:11]=[C:1]1[C:7]1[S:8][C:9]2[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[CH:13]=[CH:12][C:10]=2[N:11]=1

Participants

6

Reactant 3

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

Product 1

HCID 59626036HCID 59626036, compoundYield 186.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-phenyl-benzothiazole-6-carboxylate 9q (130 mg, 0.45 mmol) was stirred with LiOH (43 mg, 1.8 mmol) in THF (4 mL) and H2O (2 mL) for 6 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 9r (110 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-3e89f6af4775470cae0dce96318744bc
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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