Dimethyl Sulfide → 4-Chloro-5-(3-hydroxybenzylamino)-2-i-propyl-3-(2H)pyridazinone

HRID 2372348Notes

Reaction equation

HRID 2372348 reaction equation
[Cl:1][C:2]1[C:3](=[O:27])[N:4]([CH:24]([CH3:26])[CH3:25])[N:5]=[CH:6][C:7]=1[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16]CC2C=CC=CC=2)[CH:11]=1.CSC.ClCCl.B(F)(F)F.CCOCC>CCCCCC>[Cl:1][C:2]1[C:3](=[O:27])[N:4]([CH:24]([CH3:25])[CH3:26])[N:5]=[CH:6][C:7]=1[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 138538954-chloro-5-(3-benzyloxybenzylamino)-2-i-propyl-3(2H)pyridazinone

Product 1

HCID 138538984-Chloro-5-(3-hydroxybenzylamino)-2-i-propyl-3-(2H)pyridazinone

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a mixture comprising 1.15 g of 4-chloro-5-(3-benzyloxybenzylamino)-2-i-propyl-3(2H)pyridazinone (Compound No. 95) prepared in Example 1A, 10 ml of dimethyl sulfide and 4 ml of dichloromethane, 3.41 g of boron trifluoride etherate was added under cooling with ice. The mixture was stirred at 0° C. for 30 minutes and at room temperature for further 24 hours. The reaction solution was cooled with ice and 40 ml of n-hexane was added thereto, whereby a pale yellow solid substance was precipitated. The solid substance was collected by filtration, and washed with n-hexane, and then treated with ethyl acetate and water. The organic layer was separated, and washed with water and a saturated sodium chloride aqueous solution, and dried over sodium sulfate, and then the solvent was distilled off to obtain a pale yellow solid substance. This substance was crystallized from ethyl acetate-ether to obtain 730 mg of the above identified compound having a melting point of from 194.5 to 196° C. as colorless crystals.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. additionwas added
  4. customwhereby a pale yellow solid substance was precipitated
  5. filtrationThe solid substance was collected by filtration
  6. washwashed with n-hexane
  7. additiontreated with ethyl acetate and water
  8. customThe organic layer was separated
  9. washwashed with water
  10. dry with materiala saturated sodium chloride aqueous solution, and dried over sodium sulfate
  11. distillationthe solvent was distilled off
  12. customto obtain a pale yellow solid substance
  13. customThis substance was crystallized from ethyl acetate-ether
  14. customto obtain 730 mg of the
  15. customof from 194.5 to 196° C.

Sources & evidence

ORD record
ord-ef98a7fd25a647979111dd283f59890a
Source dataset
uspto-grants-1992_03
Patent number
US05098900

Reaction notes

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