Pyridine → HCID 14302784, compound

HRID 2231689Notes

Reaction equation

HRID 2231689 reaction equation
[Br:1][C:2]1[C:3](=[O:28])[N:4]([CH2:26][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)[NH2:20])=[CH:15][C:14]=1[CH2:22][CH2:23][CH2:24][CH3:25].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.N1C=CC=CC=1>CN(C)C=O>[Br:1][C:2]1[C:3](=[O:28])[N:4]([CH2:26][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]#[N:20])=[CH:15][C:14]=1[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 13987802HCID 13987802, compound

Product 1

HCID 14302784HCID 14302784, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture comprising 316 mg of 4-bromo-5-[3-(2-n-butyl-4-carbamoylphenoxy)propylamino]-2-ethyl-3(2H) pyridazinone (Compound No. 180), 174 mg of p-toluenesulfonyl chloride, 110 mg of pyridine and 5 ml of N,N-dimethylformamide, was stirred at 95° C. for 1.5 hours. The reaction mixture was subjected to distillation under reduced pressure. Water was poured into the residual oily substance, and the mixture was extracted with ethyl acetate. The extract was washed sequentially with 5% dilute hydrochloric acid, water and a saturated sodium hydrogen carbonate aqueous solution, and dried over sodium sulfate. Then, the solvent was distilled off to obtain a pale yellow oily substance. The oily substance was crystallized from ethyl ether to obtain 248 mg of the above identified compound as colorless crystals having a melting point of from 107.5° to 108.5° C.

Workup

  1. distillationThe reaction mixture was subjected to distillation under reduced pressure
  2. additionWater was poured into the residual oily substance
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed sequentially with 5% dilute hydrochloric acid, water
  5. dry with materiala saturated sodium hydrogen carbonate aqueous solution, and dried over sodium sulfate
  6. distillationThen, the solvent was distilled off
  7. customto obtain a pale yellow oily substance
  8. customThe oily substance was crystallized from ethyl ether
  9. customto obtain 248 mg of the
  10. customof from 107.5° to 108.5° C.

Sources & evidence

ORD record
ord-4493f5abed4540d191b2715c10fe1c3a
Source dataset
uspto-grants-1988_11
Patent number
US04783462

Reaction notes

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