Phenylacetic Acid → HCID 22648251, compound

HRID 1199981Notes

Reaction equation

HRID 1199981 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]1([CH2:19][C:20](O)=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>>[CH2:19]([C:20]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)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 999Phenylacetic AcidHCID 14798Sodium HydroxideHCID 1785079903-Aminoquinoline-4-thiol

Product 1

HCID 22648251HCID 22648251, compoundYield 60%

Conditions

Temperature
140 °C

Procedure

A mixture of 17.62 g (0.1 mole) of 3-amino-4-mercapto-quinoline, 15 g (0.11 mole) of phenyl acetic acid and 200 g of polyphosphoric acid is slowly heated to 140° C. under stirring. The reaction mixture is allowed to stand at this temperature for 2 hours, cooled and added to 1000 g of crushed ice under vigorous stirring. The mixture is made alkaline with an aqueous sodium hydroxide solution, extracted three times with 250 ml of chloroform each and the chloroform extract is evaporated. Thus 16.5 g of 2-benzyl-thiazolo[4,5-c]quinoline are obtained, m.p.: 111°-113° C., yield 60%.

Workup

  1. temperaturecooled
  2. extractionextracted three times with 250 ml of chloroform each and the chloroform
  3. extractionextract
  4. customis evaporated

Sources & evidence

ORD record
ord-93428c4ea80b400ab5efa0fe14e028a0
Source dataset
uspto-grants-1990_02
Patent number
US04904669

Reaction notes

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