Methanol → 2-Sulfanyl-1,3-benzoxazole-6-carboxylic acid

HRID 2041005Notes

Reaction equation

HRID 2041005 reaction equation
[S:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([O:13]C)=[O:12])=[CH:10][C:4]=2[O:3]1.[OH-].[K+].O1CCCC1.CO>C(OCC)(=O)C.O>[S:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:4]=2[O:3]1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 45789990Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate

Product 1

HCID 207347702-Sulfanyl-1,3-benzoxazole-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

Methyl 2-thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxylate (Example 92A, 470 mg, 2.25 mmol) and potassium hydroxide (1.26 g, 22.5 mmol) were combined in a 11.6 mL mixture of tetrahydrofuran, methanol, and water (10:1:1) and stirred at 45° C. for three hours. The reaction mixture was diluted with ethyl acetate, washed with a 1 N aqueous solution of hydrochloric acid, dried over sodium sulfate, and concentrated under reduced pressure to afford the title compound. MS (ESI−) m/z 193.8 (M−H)−.

Workup

  1. washwashed with a 1 N aqueous solution of hydrochloric acid
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-32c51171f5bd4009a0e07d91c49a0821
Source dataset
uspto-grants-2013_11
Patent number
US08580968B2

Reaction notes

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