Water → HCID 71655736, compound

HRID 1503206Notes

Reaction equation

HRID 1503206 reaction equation
[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12](/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.O>ClCCl>[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12]([CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471Triethylamine2×HCID 71655737HCID 71655737, compound

Product 1

HCID 71655736HCID 71655736, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (10 ml) of 3,4-bis(benzyloxy)-6-[(E)-2-(4-chlorophenyl)vinyl]pyridazine (200 mg) in dichloromethane were added triethylamine (200 μL) and 2,4,6-triisopropylbenzenesulfonylhydrazide (700 mg), and the mixture was stirred at room temperature for 40 hr. Triethylamine (200 μL) and 2,4,6-triisopropylbenzenesulfonylhydrazide (700 mg) were added, and the mixture was further stirred at room temperature for 24 hr. Water was added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 3,4-bis(benzyloxy)-6-[2-(4-chlorophenyl)ethyl]pyridazine (70 mg).

Workup

  1. stirringthe mixture was further stirred at room temperature for 24 hr
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationthe solvent was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1591e1ef95c24a4d9c31f372a1ccc12e
Source dataset
uspto-grants-2015_12
Patent number
US09212147B2

Reaction notes

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