Sodium Hydroxide → HCID 19864500, compound

HRID 1199980Notes

Reaction equation

HRID 1199980 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[SH:15])=[CH:12][CH:11]=[C:10]([Cl:16])[CH:9]=2)(=O)[CH3:2].[OH-].[Na+]>O>[Cl:16][C:10]1[CH:11]=[CH:12][C:13]2[C:14]3[S:15][C:1]([CH3:2])=[N:4][C:5]=3[CH:6]=[N:7][C:8]=2[CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178474361HCID 178474361, compound

Product 1

HCID 19864500HCID 19864500, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 12.56 g (0.05 mole) of 3-acetamido-7-chloro-4-mercapto-quinoline and 120 g of polyphosphoric acid is heated to 140°-160° C. The reaction mixture is stirred at this temperature for 2 hours, cooled to 90° C., whereupon 700 ml of water are added under vigorous stirring. When the reaction mixture has cooled to 20° C., it is made alkaline by adding a sodium hydroxide solution. The resulting mixture comprising a precipitate is extracted three times with 150 ml of chloroform each. The chloroform layers are united and evaporated to 60 ml, whereupon 300 ml of ethanol are added. 9.3 g of 7-chloro-2-methyl-thiazolo[4,5-c]quinoline are obtained in the form of needle crystals. Yield 80%, m.p.: 181°-183° C.

Workup

  1. temperatureis heated to 140°-160° C
  2. additionare added under vigorous stirring
  3. extractionis extracted three times with 150 ml of chloroform each
  4. customevaporated to 60 ml, whereupon 300 ml of ethanol
  5. additionare added

Sources & evidence

ORD record
ord-f1916c1da4674d9e9b88060a3c09d428
Source dataset
uspto-grants-1990_02
Patent number
US04904669

Reaction notes

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