Propyl sulfide → HCID 13987756, compound

HRID 2231690Notes

Reaction equation

HRID 2231690 reaction equation
[Cl:1][C:2]1[C:3](=[O:26])[N:4]([CH2:24][CH3:25])[N:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][C:14]=1[CH2:21][CH2:22][CH3:23].[Cl-].[Al+3].[Cl-].[Cl-].C(SCCC)CC>C(Cl)Cl>[Cl:1][C:2]1[C:3](=[O:26])[N:4]([CH2:24][CH3:25])[N:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=1[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 8118Propyl sulfideHCID 6451240Aluminum(III) Chloride2×HCID 13987736HCID 13987736, compound

Product 1

HCID 13987756HCID 13987756, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution obtained by dissolving 0.35 g of 4-chloro-5-[3-(2-n-propyl-4-methoxyphenoxy)propylamino]-2-ethyl-3(2H)pyridazinone (Compound No. 82) in 10 ml of methylene chloride, was dropwise added to a mixture comprising 0.36 g of aluminum chloride, 0.44 g of di-n-propylsulfide and 15 ml of methylene chloride, under stirring and cooling with ice. After the completion of the dropwise addition, the mixture was stirred at 0° C. for 2 hours, and then left to stand overnight in a refrigerator. Ice pieces were gradually added to the mixture to decompose excess aluminum chloride, and the mixture was extracted with chloroform. The extract was washed with water and dried over sodium sulfate. Then, the solvent was distilled off, and the residue thereby obtained, was crystallized from ethyl ether-n-hexane to obtain 0.26 g of the above identified compound as colorless crystals having a melting point of from 112° to 112.5° C.

Workup

  1. customA solution obtained
  2. temperaturecooling with ice
  3. additionAfter the completion of the dropwise addition
  4. stirringthe mixture was stirred at 0° C. for 2 hours
  5. waitleft
  6. additionIce pieces were gradually added to the mixture
  7. extractionthe mixture was extracted with chloroform
  8. washThe extract was washed with water
  9. dry with materialdried over sodium sulfate
  10. distillationThen, the solvent was distilled off
  11. customthe residue thereby obtained
  12. customwas crystallized from ethyl ether-n-hexane
  13. customto obtain 0.26 g of the
  14. customof from 112° to 112.5° C.

Sources & evidence

ORD record
ord-1d21993ca1f8412393efa266028c5ebc
Source dataset
uspto-grants-1988_11
Patent number
US04783462

Reaction notes

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