Hydrochloric Acid → HCID 12043507, compound

HRID 2296810Notes

Reaction equation

HRID 2296810 reaction equation
[CH:1]([S:4][C:5]1[S:6][C:7]([C:18]([O:20]CC)=[O:19])=[C:8]2[CH2:17][CH2:16][C:11]3[N:12]=[C:13]([CH3:15])[O:14][C:10]=3[C:9]=12)([CH3:3])[CH3:2].[OH-].[Na+].O.Cl>C(O)C>[CH:1]([S:4][C:5]1[S:6][C:7]([C:18]([OH:20])=[O:19])=[C:8]2[CH2:17][CH2:16][C:11]3[N:12]=[C:13]([CH3:15])[O:14][C:10]=3[C:9]=12)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 15885623HCID 15885623, compound

Product 1

HCID 12043507HCID 12043507, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 4,5-dihydro-8-isopropylthio-2-methylthieno[3,4-g]benzoxazole-6-carboxylate (0.71 g) was dissolved in ethanol (30 ml); a 2 N aqueous solution of sodium hydroxide (2.1 ml) was added at 50° C. After the reaction mixture was stirred at 50° C. for 1 hour, the solution obtained was poured over water, acidified with 1 N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and dried (MgSO4), after which the solvent was distilled off to yield 4,5-dihydro-8-isopropylthio-2-methylthieno[3,4-g]benzoxazole-6-carboxylic acid (0.57 g, 66%), which was then recrystallized from ethyl acetate-hexane. Yellow prisms. Melting point 277-278° C.

Workup

  1. customthe solution obtained
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-d15d3c6e42784e67b417125d01ba2b41
Source dataset
uspto-grants-2002_12
Patent number
US06489351B1

Reaction notes

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