4-Toluenesulfonyl chloride → HCID 86752876, compound

HRID 965407Notes

Reaction equation

HRID 965407 reaction equation
C(N(CC)CC)C.[C:8](=[N:11][OH:12])([NH2:10])[CH3:9].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>O1CCCC1>[C:8](=[N:11][OH:12])([NH2:10])[CH3:9].[S:19]([C:16]1[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=1)([O-:12])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 30926N-Hydroxyacetamidine

Product 1

HCID 86752876HCID 86752876, compoundYield 130.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (3 ml, 2.18 g, 0.022 mol) was added to acetamide oxime (1.5 g, 0.02 mol) in tetrahydrofuran (THF) (45 ml). To the mixture, p-toluenesulfonyl chloride (Tosylchloride, TsCl) (4.2 g, 0.022 mol) was added in small portions (generating heat intensively). The mixture was allowed to react at room temperature for 45 mins. and the precipitates were collected by filtration. THF was distilled off under reduced pressure, and water was added to the resultant residue. The residue was extracted with ethyl acetate, and the organic layer was washed with water and dried over sodium sulfate. The ethyl acetate was distilled off under reduced pressure, and isopropyl ether was added to the residue to separate crystals. The crystals were filtered off is and dried to give acetamide-oxime-tosylate (3.2 g, yield; 69.2%).

Workup

  1. temperaturegenerating heat intensively)
  2. customto react at room temperature for 45 mins
  3. filtrationand the precipitates were collected by filtration
  4. distillationTHF was distilled off under reduced pressure, and water
  5. additionwas added to the resultant residue
  6. extractionThe residue was extracted with ethyl acetate
  7. washthe organic layer was washed with water
  8. dry with materialdried over sodium sulfate
  9. distillationThe ethyl acetate was distilled off under reduced pressure, and isopropyl ether
  10. additionwas added to the residue
  11. customto separate crystals
  12. filtrationThe crystals were filtered off
  13. customdried

Sources & evidence

ORD record
ord-6681cfa0b13947e59caa2063f893b74c
Source dataset
uspto-grants-1998_06
Patent number
US05773624

Reaction notes

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