Hydrochloric Acid → 4-Amino-2-benzamidothiazole-5-carboxylic Acid

HRID 45312Notes

Reaction equation

HRID 45312 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([NH:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:5][C:6]=1[C:7]([O:9]C)=[O:8].O.[OH-].[Li+].Cl>O1CCCC1.O>[NH2:1][C:2]1[N:3]=[C:4]([NH:11][C:12](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[S:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86642511Methyl 4-amino-2-benzamidothiazole-5-carboxylate

Product 1

HCID 866425124-Amino-2-benzamidothiazole-5-carboxylic AcidYield 93.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-amino-2-benzamidothiazole-5-carboxylate (0.16 g, 0.57 mmol) in tetrahydrofuran (10 mL) and water (5 mL) was added lithium hydroxide monohydrate (0.007 g, 1.60 mmol). The reaction mixture was stirred at ambient temperature for 16 hours and adjusted to pH 5˜6 with 5% hydrochloric acid. The mixture was extracted with ethyl acetate (3×100 mL) and the combined organic extract was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to afford the title compound (0.14 g, 88%); MS (ES+) m/z 263.4 (M+1).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
  2. extractionthe combined organic extract
  3. washwas washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-dc619ad999cc4981a0aa6c422f1f4824
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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