Hydrochloric Acid → 2-(2'-Hydroxystyryl)benzothiazole

HRID 460596

Reaction equation

HRID 460596 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH3:10][C:11]1[S:12][CH:13]=[CH:14][N:15]=1.Cl.[OH-].[K+]>>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[CH:10][C:11]1[S:12][C:13]2[CH:7]=[CH:8][CH:2]=[CH:1][C:14]=2[N:15]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6998SalicylaldehydeHCID 14797Potassium HydroxideHCID 771292-Methylthiazole

Product 1

HCID 1363860142-(2'-Hydroxystyryl)benzothiazoleYield 39.5%

Conditions

Temperature
100 °C

Procedure

Salicylaldehyde (6.1 g) and 2-methylthiazole (7.5 g) were mixed and conc. hydrochloric acid (1.5 ml) was added thereto. The mixture was stirred with heating at 100° C. for 9 hr. The reaction mixture was cooled, and aqueous potassium hydroxide solution was added. The aqueous layer was washed with ether and made acidic with hydrochloric acid and extracted again with ethyl acetate. The organic solvent was dried and concentrated to give the title compound (2.5 g) as pale-yellow crystals, melting point 235–236° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washThe aqueous layer was washed with ether
  3. extractionextracted again with ethyl acetate
  4. customThe organic solvent was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b04f09153a054cb38c7b09b8f16fa783
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Linked notes

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