Dichloromethane → HCID 13987668, compound

HRID 2231681Notes

Reaction equation

HRID 2231681 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]([C:24]([CH3:27])([CH3:26])[CH3:25])[N:16]=[CH:17][C:18]=1[NH:19][CH2:20][CH2:21][CH2:22][OH:23].ClCCl>N1C=CC=CC=1>[Cl:12][C:13]1[C:14](=[O:28])[N:15]([C:24]([CH3:25])([CH3:27])[CH3:26])[N:16]=[CH:17][C:18]=1[NH:19][CH2:20][CH2:21][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

5

Reactant 3

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chloride2×HCID 13987664HCID 13987664, compound

Product 1

HCID 13987668HCID 13987668, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

2.55 g of p-toluenesulfonyl chloride was added to a mixture comprising 3.16 g of 4-chloro-5-(3-hydroxypropylamino)-2-t-butyl-3(2H) pyridazinone prepared in Reference Example 4, 1.44 g of pyridine and 50 ml of dichloromethane under stirring and cooling with ice, and the mixture was stirred at the same temperature for 2 hours. Then, 2.0 g of pyridine and 2.5 g of p-toluenesulfonyl chloride were added to the reaction mixture in this order. The mixture was stirred for further 2 hours under cooling with ice, and left to stand overnight in an ice chamber. The solvent was distilled off, and the pale yellow oily substance thereby obtained was extracted with benzene. The extract was washed sequentially with dilute hydrochloric acid, water (twice) and a saturated sodium chloride aqueous solution, and dried over sodium sulfate. Then, solvent was distilled off to obtain a pale yellow oily substance. The oily substance was purified by silica gel column chromatography by using benzene-ethyl acetate (1:1, v/v) as the developer, to obtain 4.67 g of the above identified compound as a pale yellow viscous oily substance.

Workup

  1. temperaturecooling with ice
  2. stirringthe mixture was stirred at the same temperature for 2 hours
  3. stirringThe mixture was stirred for further 2 hours
  4. temperatureunder cooling with ice
  5. waitleft
  6. distillationThe solvent was distilled off
  7. customthe pale yellow oily substance thereby obtained
  8. extractionwas extracted with benzene
  9. washThe extract was washed sequentially with dilute hydrochloric acid, water (twice) and a saturated sodium chloride aqueous solution
  10. dry with materialdried over sodium sulfate
  11. distillationThen, solvent was distilled off
  12. customto obtain a pale yellow oily substance
  13. customThe oily substance was purified by silica gel column chromatography
  14. customv/v) as the developer, to obtain 4.67 g of the

Sources & evidence

ORD record
ord-7bf8f900675541549f1258bee85610ae
Source dataset
uspto-grants-1988_11
Patent number
US04783462

Reaction notes

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