Hydrochloric Acid → HCID 21285477, compound

HRID 2231684Notes

Reaction equation

HRID 2231684 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:12][C:13]1[C:14](=[O:28])[N:15]([CH:25]([CH3:27])[CH3:26])[N:16]=[CH:17][C:18]=1[NH:19][CH2:20][CH:21]([OH:24])[CH2:22][OH:23].N1C=CC=CC=1.Cl>ClCCl>[Cl:12][C:13]1[C:14](=[O:28])[N:15]([CH:25]([CH3:26])[CH3:27])[N:16]=[CH:17][C:18]=1[NH:19][CH2:20][CH:21]([OH:24])[CH2:22][O:23][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 13987839HCID 13987839, compound

Product 1

HCID 21285477HCID 21285477, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.60 g of p-toluenesulfonyl chloride was added to a mixture comprising 2.09 g of 4-chloro-5-(2,3-dihydroxypropylamino)-2-i-propyl-3(2H)pyridazinone prepared in Reference Example 6, 12 ml of pyridine and 20 ml of dichloromethane, under cooling with ice. The mixture was stirred for 6 hours, and then left to stand for 2 days in an ice chamber. The reaction mixture was acidified to a pH of about 2 by adding cooled dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed sequentially with water, a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution, and dried over sodium sulfate. Then, the solvent was distilled off to obtain a colorless oily substance. The oily substance was purified by silica gel column chromatography, and 2.45 g of the above identified compound was obtained as a colorless viscous oily substance from the eluate with choroform-methanol (25:1, v/v).

Workup

  1. temperatureunder cooling with ice
  2. waitleft
  3. additionby adding
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed sequentially with water
  6. dry with materiala saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution, and dried over sodium sulfate
  7. distillationThen, the solvent was distilled off
  8. customto obtain a colorless oily substance
  9. customThe oily substance was purified by silica gel column chromatography, and 2.45 g of the
  10. customwas obtained as a colorless viscous oily substance from the eluate with choroform-methanol (25:1

Sources & evidence

ORD record
ord-d1a6004969b14a32a6dca694b22eeabd
Source dataset
uspto-grants-1988_11
Patent number
US04783462

Reaction notes

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