Hydrochloric Acid → 4-(1,3-Thiazol-2-yl)benzoic acid

HRID 1373246Notes

Reaction equation

HRID 1373246 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.Cl([O-])=[O:15].[Na+].P([O-])(O)(O)=O.[Na+].CC(=CC)C.Cl>O.O1CCCC1.C(O)(C)(C)C>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([C:10]([OH:15])=[O:11])=[CH:12][CH:13]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 105356554-(1,3-Thiazol-2-yl)benzaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 235104714-(1,3-Thiazol-2-yl)benzoic acidYield 81.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(2-thiazolyl)benzaldehyde (4.6 g, 24 mmol), sodium chlorite (5.5 g, 61 mmols), sodium dihydrogenphosphate (3.2 g, 27 mmols), 2-methyl-2-butene (8.6 g, 120 mmols), tert-butanol (40 ml), tetrahydrofuran (40 ml) and water (20 ml) was stirred at room temperature for 3 hours. The mixture was poured into 1 N hydrochloric acid, and the precipitate formed was taken out through filtration and dried. Thus was obtained a solid of 4-(2-thiazolyl)benzoic acid (4.0 g, 79%).

Workup

  1. customthe precipitate formed
  2. filtrationwas taken out through filtration
  3. customdried

Sources & evidence

ORD record
ord-bb35a1fc6d944a90a10a750cd7c3456a
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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