Butyl iodide → HCID 86613947, compound

HRID 1811447Notes

Reaction equation

HRID 1811447 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([N:14]1[C:23]2[C:18](=[C:19]([CH2:25][CH:26]3[S:30][C:29](=[O:31])[NH:28][C:27]3=[O:32])[CH:20]=[CH:21][C:22]=2[OH:24])[CH2:17][CH2:16][C:15]1=[O:33])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.I[CH2:35][CH2:36][CH2:37][CH3:38].S([O-])(O)(=O)=O.[K+]>O.CS(C)=O>[CH2:7]([N:14]1[C:23]2[C:18](=[C:19]([CH2:25][CH:26]3[S:30][C:29](=[O:31])[NH:28][C:27]3=[O:32])[CH:20]=[CH:21][C:22]=2[O:24][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:17][CH2:16][C:15]1=[O:33])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 10962Butyl iodideHCID 516920Potassium bisulfateHCID 23665647Potassium tert-butoxideHCID 86613946HCID 86613946, compound

Product 1

HCID 86613947HCID 86613947, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

55.5 mg of potassium tert-butoxide was added to a DMSO solution (1 ml) of 90 mg of 5-(1-benzyl-8-hydroxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl)thiazolidine-2,4-dione, followed by stirring at room temperature for 1 hour. 29.8 μl of 4-iodobutane was added thereto, followed by stirring at room temperature for 2 hours. Water was added to the reaction liquid, potassium hydrogensulfate was added to the mixture, and the mixture was extracted with ethyl acetate. After washing with water, the extract was dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by preparative silica gel thin layer chromatography (dichloromethane:methanol=20:1), giving 42 mg (41% yield) of 5-(1-benzyl-8-butoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl)thiazolidine-2,4-dione as a colorless amorphous solid.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. additionwas added to the mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washAfter washing with water
  5. dry with materialthe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by preparative silica gel thin layer chromatography (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-808bf95ecf9343a9b55e4eaf131fb2cf
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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