Hydrochloric Acid → HCID 12043507, compound

HRID 1936877Notes

Reaction equation

HRID 1936877 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-f8c181d0bd8b40289ab5c5d4893b691e
Source dataset
uspto-grants-2002_05
Patent number
US06391905B1

Reaction notes

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