Hydrochloric Acid → 2-(Benzo[d]thiazol-2-yloxy)acetic acid

HRID 1404942Notes

Reaction equation

HRID 1404942 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][CH2:11][C:12]([O:14]CC)=[O:13].[OH-].[Na+].Cl>CO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59467898HCID 59467898, compound

Product 1

HCID 2435072-(Benzo[d]thiazol-2-yloxy)acetic acidYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 60 (1.32 g, 5.6 mmol) in MeOH was added NaOH (3M, 75 mL, 0.22 mol) dropwise. The mixture was stirred at room temperature over night. It was then cooled in an ice-water bath and acidified to pH<2 with HCl (2N). The mixture was then extracted with CHCl3 (3×). The combined organic layers were dried over Na2SO4 and concentrated in vacuum to yield 61 as a white solid (1.0 g, 86%).

Workup

  1. temperatureIt was then cooled in an ice-water bath
  2. extractionThe mixture was then extracted with CHCl3 (3×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-506823504202427ba8fc1d607fb1f1c8
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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