Hexane → HCID 68507420, compound

HRID 1949156Notes

Reaction equation

HRID 1949156 reaction equation
[CH3:1]C([O-])(C)C.[K+].[CH3:7][O:8][C:9](=[O:13])[CH2:10][CH2:11][SH:12].[CH2:14]([O:16][C:17]([C:19]1[C:20](Cl)=[N:21][C:22]2[C:27]([C:28]=1[CH3:29])=[CH:26][CH:25]=[C:24]([C:30]([F:33])([F:32])[F:31])[CH:23]=2)=[O:18])[CH3:15].CCCCCC>CN(C=O)C.O>[CH2:14]([O:16][C:17]([C:19]1[C:20]([S:12][CH2:11][CH2:10][C:9]([O:8][CH2:7][CH3:1])=[O:13])=[N:21][C:22]2[C:27]([C:28]=1[CH3:29])=[CH:26][CH:25]=[C:24]([C:30]([F:33])([F:32])[F:31])[CH:23]=2)=[O:18])[CH3:15]

Participants

7

Reactant 4

HCID 8058HexaneHCID 18050Methyl 3-mercaptopropionateHCID 23665647Potassium tert-butoxideHCID 866453402-Chloro-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 68507420HCID 68507420, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

336 mg (3.0 mmol) potassium tert-butylate were added to a solution of 360 mg (3.0 mmol) 3-mercaptopropionic acid methyl ester in DMF (8 ml) at 0° C. and the mixture was stirred for 30 min at 0° C. Then 953 mg (3.0 mmol) 2-chloro-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester were added and the reaction solution was heated slowly to 50° C. and stirred for 16 h at this temperature. After cooling to RT the mixture was diluted with water and extracted with EE. The organic phase was dried over MgSO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 9:1) of the residue yielded 625 mg (1.5 mmol, 50%) 2-(3-ethoxy-3-oxopropylthio)-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester.

Workup

  1. temperaturethe reaction solution was heated slowly to 50° C.
  2. stirringstirred for 16 h at this temperature
  3. temperatureAfter cooling to RT the mixture
  4. extractionextracted with EE
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-8dd2f91ceceb464dad5c6f9a54f98b7b
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

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