Ammonia → HCID 13987762, compound

HRID 2231688Notes

Reaction equation

HRID 2231688 reaction equation
[Cl:1][C:2]1[C:3](=[O:29])[N:4]([CH:26]([CH3:28])[CH3:27])[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]([C:19](O)=[O:20])=[CH:15][C:14]=1[CH2:22][CH2:23][CH2:24][CH3:25].S(Cl)(Cl)=O.[NH3:34]>O1CCCC1>[Cl:1][C:2]1[C:3](=[O:29])[N:4]([CH:26]([CH3:28])[CH3:27])[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]([C:19](=[O:20])[NH2:34])=[CH:15][C:14]=1[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 13987760HCID 13987760, compound

Product 1

HCID 13987762HCID 13987762, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture comprising 168 mg of 4-chloro-5-[3-(2-n-butyl-4-carboxyphenoxy)propylamino]-2-i-propyl-3(2H) pyridazinone (Compound No. 112), 119 mg of thionyl chloride and 10 ml of dried tetrahydrofuran, was refluxed under stirring for 1 hour. The reaction mixture was subjected to distillation under reduced pressure. To the residue, 20 ml of dried benzene was added. The mixture was again subjected to distillation under reduced pressure to remove excess thionyl chloride by azeotropic distillation. The residual oily substance thereby obtained, was dissolved in 10 ml of dried tetrahydrofuran, and ammonia gas was introduced thereinto for 5 minutes under cooling with ice. Then, the reaction solution was further stirred for 15 minutes. The reaction mixture was subjected to distillation under reduced pressure, and water was poured into the residue thereby obtained. The mixture was extracted with chloroform. The extract was washed sequentially with a 5% sodium hydroxide aqueous solution and a saturated sodium chloride aqueous solution, and dried over sodium sulfate. Then, the solvent was distilled off, and a pale yellow oily substance thereby obtained was crystallized from methanol-ethyl ether to obtain 143 mg of the above identified compound as colorless crystals having a melting point of 172° to 174° C.

Workup

  1. distillationThe reaction mixture was subjected to distillation under reduced pressure
  2. additionTo the residue, 20 ml of dried benzene was added
  3. distillationThe mixture was again subjected to distillation under reduced pressure
  4. customto remove excess thionyl chloride
  5. distillationby azeotropic distillation
  6. customThe residual oily substance thereby obtained
  7. temperaturefor 5 minutes under cooling with ice
  8. stirringThen, the reaction solution was further stirred for 15 minutes
  9. distillationThe reaction mixture was subjected to distillation under reduced pressure, and water
  10. additionwas poured into the residue
  11. customthereby obtained
  12. extractionThe mixture was extracted with chloroform
  13. washThe extract was washed sequentially with a 5% sodium hydroxide aqueous solution
  14. dry with materiala saturated sodium chloride aqueous solution, and dried over sodium sulfate
  15. distillationThen, the solvent was distilled off
  16. customa pale yellow oily substance thereby obtained
  17. customwas crystallized from methanol-ethyl ether
  18. customto obtain 143 mg of the

Sources & evidence

ORD record
ord-4d06d94370e1485795be8f1f2abbe4cd
Source dataset
uspto-grants-1988_11
Patent number
US04783462

Reaction notes

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