Diethyl Sulfate → HCID 15006891, compound

HRID 1649871Notes

Reaction equation

HRID 1649871 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.S(OCC)(O[CH2:18][CH3:19])(=O)=O>[OH-].[Na+]>[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[S:12][CH2:18][CH3:19])=[CH:9][CH:8]=[C:7]([Cl:13])[CH:6]=2

Participants

4

Reactant 2

HCID 6163Diethyl SulfateHCID 178507997HCID 178507997, compound

Product 1

HCID 15006891HCID 15006891, compoundYield 85%

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 19.27 g (0.125 mole) of diethyl sulfate are added. The reaction mixture is heated to boiling for 2 hours, cooled to room temperature and extracted with dichloro ethane. The dichloro ethane solution is dried, clarified and evaporated. Thus 20.2 g of 3-amino-4-ethylthio-7-chloro-quinoline are obtained, yield 85%, m.p.: 105°-106° C. (after crystallization from methanol).

Workup

  1. additionare added
  2. temperatureThe reaction mixture is heated
  3. extractionextracted with dichloro ethane
  4. dry with materialThe dichloro ethane solution is dried
  5. customevaporated

Sources & evidence

ORD record
ord-053c5397dc2b4dd0a5531ecbcaf7a102
Source dataset
uspto-grants-1990_05
Patent number
US04921960

Reaction notes

Loading…