Hydrochloric Acid → HCID 13015767, compound

HRID 568618Notes

Reaction equation

HRID 568618 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][O:6][C:7]1[CH:21]=[CH:20][C:10]2[C:11]([C:14]3[S:15][C:16]([CH3:19])=[CH:17][CH:18]=3)=[N:12][O:13][C:9]=2[C:8]=1[Cl:22])C.[OH-].[Na+].Cl>C(O)C>[Cl:22][C:8]1[C:9]2[O:13][N:12]=[C:11]([C:14]3[S:15][C:16]([CH3:19])=[CH:17][CH:18]=3)[C:10]=2[CH:20]=[CH:21][C:7]=1[O:6][CH2:5][C:4]([OH:23])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14012479HCID 14012479, compound

Product 1

HCID 13015767HCID 13015767, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 15.0 g of ethyl{[7-chloro-3-(5-methyl-2-thienyl)-1,2-benzisoxazole-6-yl]oxy}acetate of Example 9b and 10 ml of 50% NaOH in 800 ml of ethanol is refluxed for 30 minutes and then 100 ml of 5% HCl is added, making the solution homogeneous. A product begins to crystallize as the solution cools and additional water is added. The product is filtered off and recrystallized form isopropanol giving {[7-chloro-3-(5-methyl-2-thienyl)-1,2-benzisoxazol-6-yl]oxy}acetic acid, mp 235°-238° C.

Workup

  1. temperatureis refluxed for 30 minutes
  2. customto crystallize as the solution cools and additional water
  3. additionis added
  4. filtrationThe product is filtered off
  5. customrecrystallized form isopropanol

Sources & evidence

ORD record
ord-e3e06df02d1a4e01af1fcb9d69330ea3
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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