Hydrochloric Acid → 2-(1,1-Dimethylethyl)-5-benzothiazoleacetic acid

HRID 1264626Notes

Reaction equation

HRID 1264626 reaction equation
[C:1]([C:5]1[S:6][C:7]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]#N)=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-:17].[K+].Cl.C[OH:21]>O>[C:1]([C:5]1[S:6][C:7]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:21])=[O:17])=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 53849835HCID 53849835, compound

Product 1

HCID 186136132-(1,1-Dimethylethyl)-5-benzothiazoleacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The product from Step 5 (0.90 g, 0.004 mol) was dissolved in methanol (8 ml) and a solution of potassium hydroxide pellets (0.35 g, 0.006 mol) in water (2 ml) was added. The mixture was refluxed for 17 hours and was then cooled to room temperature. The mixture was acidified with concentrated hydrochloric acid to pH4 and the resultant solution was diluted with water and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo to afford 2-tert-butyl-5-benzothiazolylacetic acid (0.5 g) as a viscous oil.

Workup

  1. temperatureThe mixture was refluxed for 17 hours
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-0ea0485db6224d25ad3e300a17fbc6d8
Source dataset
uspto-grants-2003_04
Patent number
US06544989B2

Reaction notes

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