Phenyl thioxochloroformate → Phenyl N-(2-methylquinolin-3-yl)thiocarbamate

HRID 377900Notes

Reaction equation

HRID 377900 reaction equation
[NH2:1][C:2]1[C:3]([CH3:12])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH:13]1[CH:18]=[CH:17][C:16]([O:19][C:20](Cl)=[S:21])=[CH:15][CH:14]=1>C(Cl)Cl>[CH3:12][C:3]1[C:2]([NH:1][C:20](=[S:21])[O:19][C:16]2[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=2)=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 70498Phenyl thioxochloroformateHCID 123006962-Methylquinolin-3-amine

Product 1

HCID 53717370Phenyl N-(2-methylquinolin-3-yl)thiocarbamateYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-2-methylquinoline(4 g, 25 mmol) and phenyl chlorothionoformate(4.32 g, 25 mmol) were dissolved in methylene chloride and then was stirred at room temperature for 2 hours. The mixture solution was concentrated under reduced pressure to remove methylene chloride and purified by column chromatography(ethylacetate:hexane=1:2) to obtain the titled compound.

Workup

  1. concentrationThe mixture solution was concentrated under reduced pressure
  2. customto remove methylene chloride
  3. custompurified by column chromatography(ethylacetate:hexane=1:2)

Sources & evidence

ORD record
ord-eaff6481213d40afafe68caf7ebe3ce2
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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