Ethyl benzenesulfonate → HCID 19855243, compound

HRID 1649869Notes

Reaction equation

HRID 1649869 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]=[C:7]([Cl:13])[CH:6]=2.[C:14]1(S(OCC)(=O)=O)C=CC=C[CH:15]=1>[OH-].[Na+]>[ClH:13].[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[S:12][CH2:14][CH3:15])=[CH:9][CH:8]=[C:7]([Cl:13])[CH:6]=2

Participants

4

Reactant 2

HCID 10585Ethyl benzenesulfonateHCID 178507997HCID 178507997, compound

Product 1

HCID 19855243HCID 19855243, compoundYield 174.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

21.06 g (0.1 mole) of 3-amino-7-chloro-4-quinoline-thiol are dissolved in 100 ml of a 2 molar sodium hydroxide solution, whereupon 23.30 g (0.125 mole) of ethyl benzene sulfonate are added. The reaction mixture is heated to boiling for 2 hours and the product thus formed is extracted with chloroform. The chloroform solution is clarified with activated charcoal, dried and acidified with alcohol containing hydrogen chloride. Thus 24.0 g of 3-amino-4-ethylthio-7-chloro-quinoline-hydrochloride are obtained. After crystallization from methanol the product melts at 212°-216° C. under decomposition. Yield 85%. The product thus obtained is identical with the compound prepared according to Example 5.

Workup

  1. additionare added
  2. temperatureThe reaction mixture is heated
  3. customthe product thus formed
  4. extractionis extracted with chloroform
  5. customdried
  6. additioncontaining hydrogen chloride

Sources & evidence

ORD record
ord-917a576abd174c819801d69b7c8c55e6
Source dataset
uspto-grants-1990_05
Patent number
US04921960

Reaction notes

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