Sodium hydride → 2-tert.-butyl-4-chloro-5-[4-(1,1,2-trifluoro-2-trifluoromethoxy-ethoxy)-benzyloxy]-3(2H)-pyridazinone

HRID 1681132Notes

Reaction equation

HRID 1681132 reaction equation
[F:1][C:2]([F:19])([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=1)[CH:3]([F:9])[O:4][C:5]([F:8])([F:7])[F:6].[C:20]([N:24]1[C:29](=[O:30])[C:28]([Cl:31])=[C:27](Cl)[CH:26]=[N:25]1)([CH3:23])([CH3:22])[CH3:21].[H-].[Na+]>CN(C)C=O.CCOCC>[C:20]([N:24]1[C:29](=[O:30])[C:28]([Cl:31])=[C:27]([O:16][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][C:2]([F:19])([F:1])[CH:3]([F:9])[O:4][C:5]([F:6])([F:7])[F:8])=[CH:12][CH:13]=2)[CH:26]=[N:25]1)([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27822252-Tert-butyl-4,5-dichloro-2,3-dihydropyridazin-3-oneHCID 541155024-[1,1,2-Trifluoro-2-(trifluoromethoxy)ethoxy]benzyl alcohol

Product 1

HCID 198072032-tert.-butyl-4-chloro-5-[4-(1,1,2-trifluoro-2-trifluoromethoxy-ethoxy)-benzyloxy]-3(2H)-pyridazinoneYield 68.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

1.16 g of 4-(1,1,2-trifluoro-2-trifluoromethoxy-ethoxy)-benzyl alcohol (Example 3) and, 15 minutes later, 0.95 g of 2-tert.-butyl-4,5-dichloro-3(2H)-pyridazinone are added to a suspension of 0.2 g of sodium hydride at 50% in 10 cc of dimethylformamide. The resulting reaction mixture is stirred for 1 hour at room temperature, is diluted with ether, is washed with diluted HCl and brine; the washed solution is thoroughly dehydrated, the solvent is evaporated off and the so obtained raw reaction product is chromatographed on silica gel with 9/1 hexane/ethyl acetate. 1.3 g of pure product is obtained. Melting point 68°-69° C.

Workup

  1. customThe resulting reaction mixture
  2. washis washed with diluted HCl and brine
  3. customthe solvent is evaporated off
  4. customthe so obtained raw
  5. customreaction product
  6. customis chromatographed on silica gel with 9/1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-dc4ec62d973740c0b584fd6888ff7d19
Source dataset
uspto-grants-1992_12
Patent number
US05169848

Reaction notes

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