Sodium hydride → HCID 28413999, compound

HRID 1184405Notes

Reaction equation

HRID 1184405 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 (EI): 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-662eab6a77504922a2847084f18d11b3
Source dataset
uspto-grants-2014_03
Patent number
US08669254B2

Reaction notes

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