Ethanethiol → HCID 68513042, compound

HRID 1949162Notes

Reaction equation

HRID 1949162 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]([SH:9])[CH3:8].[CH2:10]([O:12][C:13]([C:15]1[C:16](Cl)=[N:17][C:18]2[C:23]([C:24]=1[CH3:25])=[CH:22][CH:21]=[C:20]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:19]=2)=[O:14])[CH3:11].CCCCCC>CN(C=O)C.O>[CH2:10]([O:12][C:13]([C:15]1[C:16]([S:9][CH2:7][CH3:8])=[N:17][C:18]2[C:23]([C:24]=1[CH3:25])=[CH:22][CH:21]=[C:20]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:19]=2)=[O:14])[CH3:11]

Participants

7

Reactant 4

HCID 6343EthanethiolHCID 8058HexaneHCID 11430Potassium CarbonateHCID 86645343HCID 86645343, compound

Product 1

HCID 68513042HCID 68513042, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

190 mg (1.38 mmol) K2CO3 and 100 μl (1.38 mmol) ethanethiol were added to a solution of 140 mg (0.46 mmol) 7-tert-butyl-2-chloro-4-methyl-quinoline-3-carboxylic acid ethyl ester in DMF (3 ml) and the mixture was stirred for 16 h at 60° C. Then it was diluted with water and extracted with EE. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 19:1) of the residue yielded 100 mg (0.30 mmol, 65%) 7-tert-butyl-2-ethylsulfanyl-4-methyl-quinoline-3-carboxylic acid ethyl ester.

Workup

  1. extractionextracted with EE
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-a479599245aa4738a8bbfb56d0bc48c5
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

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