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

HRID 2085168Notes

Reaction equation

HRID 2085168 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-9d7606613c5042dea87c697bd46c9e03
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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