Sodium Hydroxide → 2-Ethylthiazolo[4,5-c]quinoline

HRID 1199979Notes

Reaction equation

HRID 1199979 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[SH:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:13](OC(=O)CC)(=O)[CH2:14][CH3:15].[OH-].[Na+]>Cl>[CH2:14]([C:15]1[S:12][C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH3:13]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31263Propionic anhydrideHCID 1785079903-Aminoquinoline-4-thiol

Product 1

HCID 150279042-Ethylthiazolo[4,5-c]quinolineYield 90%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 17.62 g (0.1 mole) of 3-amino-4-mercapto-quinoline and 85 ml of propionic anhydride is first slowly heated to boiling and then refluxed for one hour and a half. The reaction mixture is added dropwise to 800 ml of 1% aqueous hydrochloric acid under vigorous stirring. The homogenous solution is made alkaline to pH 10 by adding sodium hydroxide solution and extracted three times with 200 ml of benzene each. The benzene solution is evaporated. Thus 19.26 g of 2-ethylthiazolo[4,5-c]quinoline are obtained, yield 90%, m.p.: 48°-49° C.

Workup

  1. temperatureis first slowly heated
  2. temperaturerefluxed for one hour
  3. extractionextracted three times with 200 ml of benzene each
  4. customThe benzene solution is evaporated

Sources & evidence

ORD record
ord-23e264946d404672b45bc35b0d549f8a
Source dataset
uspto-grants-1990_02
Patent number
US04904669

Reaction notes

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