Acetic Anhydride → 2-Methylthiazolo[4,5-c]quinoline

HRID 868215Notes

Reaction equation

HRID 868215 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)C)(=O)[CH3:14].[OH-].[Na+]>Cl>[CH3:13][C:14]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

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 1785079903-Aminoquinoline-4-thiol

Product 1

HCID 30661292-Methylthiazolo[4,5-c]quinoline

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 17.62 g (0.1 mole) of 3-amino-4-mercapto-quinoline and 70 ml of acetic anhydride is heated slowly to the boiling point and thereafter heated to boiling for one hour and a half. The reaction mixture is cooled and 600 ml of 1% hydrochloric acid are added dropwise under vigorous stirring. The homogenous solution is made alkaline with a sodium hydroxide solution and the precipitated base is extracted three times with 100 ml of benzene each. The united benzene extracts are clarified, dried and evaporated in vacuo. Thus 2-methyl-thiazolo[4,5-c]quinoline is obtained, m.p.: 99°-100° C. (after recrystallization from a mixture of methanol and water).

Workup

  1. temperatureis heated slowly to the boiling point
  2. temperatureheated
  3. temperatureThe reaction mixture is cooled
  4. extractionthe precipitated base is extracted three times with 100 ml of benzene each
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-10f5b229c6cc42c7b79686269fff3885
Source dataset
uspto-grants-1988_10
Patent number
US04778811

Reaction notes

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