Sodium hydride → HCID 28413999, compound

HRID 1025950Notes

Reaction equation

HRID 1025950 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].[Cl:8][C:9]1[N:10]=[N:11][C:12](Cl)=[CH:13][CH:14]=1>CS(C)=O>[Cl:8][C:9]1[N:10]=[N:11][C:12]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 673313,6-DichloropyridazineHCID 75644Cyclopropanemethanol

Product 1

HCID 28413999HCID 28413999, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 1.016 mL cyclopropanemethanol in 10 mL dimethylsulfoxide was added 0.564 g sodium hydride 55% in mineral oil and the mixture was stirred at room temperature for 15 min. The resulting solution was added drop wise to a solution of 2.0 g 3,6-dichloropyridazine in 20 mL dry dimethylsulfoxide at room temperature and stirred at this temperature for 1 h. The reaction mixture was partitioned between water and ethyl acetate, the phases were separated and the organic phase was purified by chromatography on silica gel using a gradient of heptane:ethyl acetate=95:5 to 40:60 to yield 1.88 g of the title compound as white solid, MS 185.05 (M+H)+.

Workup

  1. stirringstirred at this temperature for 1 h
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. customthe phases were separated
  4. customthe organic phase was purified by chromatography on silica gel using a gradient of heptane

Sources & evidence

ORD record
ord-7ba6b5f51fc34603838e441681f9555b
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

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