Sulfuric Acid → [3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-acetonitrile

HRID 271188Notes

Reaction equation

HRID 271188 reaction equation
[C-:1]#[N:2].[Na+].S(=O)(=O)(O)O.Br[CH2:10][C:11]1[CH:27]=[C:26]([Cl:28])[C:14]([CH2:15][C:16]2[CH:17]=[C:18]([CH:23]([CH3:25])[CH3:24])[C:19](=[O:22])[NH:20][N:21]=2)=[C:13]([Cl:29])[CH:12]=1.C(=O)(O)[O-].[Na+]>CS(C)=O.O>[Cl:29][C:13]1[CH:12]=[C:11]([CH2:10][C:1]#[N:2])[CH:27]=[C:26]([Cl:28])[C:14]=1[CH2:15][C:16]1[CH:17]=[C:18]([CH:23]([CH3:25])[CH3:24])[C:19](=[O:22])[NH:20][N:21]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 598344466-(4-Bromomethyl-2,6-dichloro-benzyl)-4-isopropyl-pyridazin-3-one

Product 1

HCID 59834478[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-acetonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

A suspension of sodium cyanide (270 mg, 5.51 mmol) in dimethyl sulfoxide (2 mL) at room temperature was treated with concentrated sulfuric acid (0.1 mL, 1.88 mmol) and a solution of 6-(4-bromomethyl-2,6-dichloro-benzyl)-4-isopropyl-pyridazin-3-one (54) (70 mg, 0.180 mmol) in dimethyl sulfoxide (2 mL). The reaction mixture was stirred at room temperature for 30 min and then at 50° C. for 1 h. The reaction was cooled to room temperature, poured into a saturated aqueous sodium bicarbonate solution (50 mL), was diluted with water (20 mL) and then extracted with ethyl acetate (3×75 mL). The organic layers were combined and washed with a saturated aqueous sodium chloride solution (50 mL), dried over magnesium sulfate, filtered, and concentrated under vacuum. The resulting oil was dried under high vacuum to afford [3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-acetonitrile (55) as an orange oil (assume 0.180 mmol) which was used without further purification.

Workup

  1. waitat 50° C. for 1 h
  2. temperatureThe reaction was cooled to room temperature
  3. extractionextracted with ethyl acetate (3×75 mL)
  4. washwashed with a saturated aqueous sodium chloride solution (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe resulting oil was dried under high vacuum

Sources & evidence

ORD record
ord-becc6acdffe7401b8adab876187bdca2
Source dataset
uspto-grants-2008_11
Patent number
US07452882B2

Reaction notes

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