Lithium Hydroxide → HCID 69313151, compound

HRID 33229Notes

Reaction equation

HRID 33229 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[CH:10]3)=[N:5][N:4]=[C:3]1[SH:17].Br[CH2:19][CH2:20][CH2:21][CH:22]1[O:27][CH2:26][C:25]([CH3:29])([CH3:28])[CH2:24][O:23]1.[OH-].[Li+]>CN(C)C=O>[CH3:28][C:25]1([CH3:29])[CH2:24][O:23][CH:22]([CH2:21][CH2:20][CH2:19][S:17][C:3]2[N:2]([CH3:1])[C:6]([C:7]3[CH:8]=[C:9]4[C:14](=[CH:15][CH:16]=3)[N:13]=[CH:12][CH:11]=[CH:10]4)=[N:5][N:4]=2)[O:27][CH2:26]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 35285702-(3-Bromopropyl)-5,5-dimethyl-1,3-dioxaneHCID 178481684HCID 178481684, compound

Product 1

HCID 69313151HCID 69313151, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Methyl-5-quinolin-6-yl-4H-[1,2,4]triazole-3-thiol (0.5 g, 2.07 mmol), 2-(3-Bromo-propyl)-5,5-dimethyl-[1,3]dioxane (0.49 g, 2.07 mmol) and lithium hydroxide (50 mg) were heated in dimethylformamide at 100° C. for 3 h. The mixture was cooled and partitioned between water (80 ml) and ethyl acetate (100 ml). The layers were separated and the aqueous re-extracted with ethyl acetate (100 ml). The combined organic portions were washed with brine (100 ml) and then dried (Na2SO4), filtered and evaporated to give a colourless oil. Purification by silica gel chromatography (eluent EtOAc—10% MeOH:EtOAc) which gave the title compound as a colourless solid (0.53 g, 65%).

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between water (80 ml) and ethyl acetate (100 ml)
  3. customThe layers were separated
  4. extractionthe aqueous re-extracted with ethyl acetate (100 ml)
  5. washThe combined organic portions were washed with brine (100 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto give a colourless oil
  10. customPurification by silica gel chromatography (eluent EtOAc—10% MeOH:EtOAc) which

Sources & evidence

ORD record
ord-06d9d6a8ad7f47798556e3ba4f535270
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Reaction notes

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