Hydrochloric Acid → 2-(3-Cyano-4-isobutyloxyphenyl)-1,3-benzothiazole-7-carboxylic acid

HRID 851868Notes

Reaction equation

HRID 851868 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:14]2(C(OC)=O)[NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[S:15]2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]([CH3:13])[CH3:12])#[N:2].[OH-].[K+].Cl.CO.[CH2:32]([OH:34])C.C1C[O:38]CC1>O>[C:1]([C:3]1[CH:4]=[C:5]([C:14]2[S:15][C:16]3[C:22]([C:32]([OH:34])=[O:38])=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]([CH3:13])[CH3:12])#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 23023851Methyl 2-(3-cyano-4-isobutyloxyphenyl)-1,3-benzothiazole-carboxylateHCID 66624091Ethanol tetrahydrofuran methanol

Product 1

HCID 121323342-(3-Cyano-4-isobutyloxyphenyl)-1,3-benzothiazole-7-carboxylic acidYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 2-(3-cyano-4-isobutyloxyphenyl)-1,3-benzothiazole-carboxylate (288 mg, 0.786 mmol) was dissolved in a mixed solvent (50 mL) of methanol/ethanol/THF (2/1/2), and, then a solution of potassium hydroxide (281 mg, 5 mmol) in water (10 mL) was added and stirred for one hour at room temperature. The mixture was made acidic by addition of aqueous 1M hydrochloric acid, and placed under reduced pressure to distill the solvent off. The residue was extracted with chloroform. The chloroform portion was then dried over anhydrous magnesium sulfate and placed under reduced pressure too distill the solvent off. The residual crystalline product was recrystallized from toluene, to give 230 mg (yield 83%) of the desired compound in the form of a white crystalline product.

Workup

  1. distillationto distill the solvent off
  2. extractionThe residue was extracted with chloroform
  3. dry with materialThe chloroform portion was then dried over anhydrous magnesium sulfate
  4. distillationtoo distill the solvent off
  5. customThe residual crystalline product was recrystallized from toluene

Sources & evidence

ORD record
ord-7dabf0aa854348f689c2c225cf01be77
Source dataset
uspto-grants-2007_08
Patent number
US07253154B2

Reaction notes

Loading…