4-Toluenesulfonyl chloride → HCID 19434013, compound

HRID 1736025Notes

Reaction equation

HRID 1736025 reaction equation
O[CH2:2][C:3]1[N:4]([CH:18]([CH3:20])[CH3:19])[S:5](=[O:17])(=[O:16])[C:6]2[S:11][C:10]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:9][C:7]=2[CH:8]=1.[CH2:21]([N:23](CC)[CH2:24][CH3:25])[CH3:22].C1(C)C=CC(S(Cl)(=O)=[O:35])=CC=1>C1COCC1>[CH3:19][CH:18]([N:4]1[C:3]([CH2:2][N:23]2[CH2:24][CH2:25][O:35][CH2:22][CH2:21]2)=[CH:8][C:7]2[CH:9]=[C:10]([S:12]([NH2:15])(=[O:14])=[O:13])[S:11][C:6]=2[S:5]1(=[O:17])=[O:16])[CH3:20]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 19434080HCID 19434080, compound

Product 1

HCID 19434013HCID 19434013, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Step E (2.16 g, 6.39 mmol) and triethylamine (2.58 g, 25.6 mmol) in anhydrous THF (100 mL) at 0° C. was added p-toluenesulfonyl chloride (2.44 g, 12.8 mmol) with stirring. After 1 h the reaction mixture was warmed to ambient temperature and maintained at this temperature for 4 h. Half of the reaction mixture was removed, cooled on an ice bath and morpholine (3 mL) was added with stirring. The reaction mixture was stirred for 18 h and evaporated to a residue which was mixed with ethyl acetate (200 mL); this solution was washed with a saturated solution of sodium bicarbonate (100 mL), dried (MgSO4), filtered and evaporated to a residue which was purified by colunmn chromatography (silica, 4% methanol/methylene chloride) to give a viscous oil which crystalized from methylene chloride/hexane to afford a yellowish solid (0.41 g, 32%): mp 196°-198° C. Analysis: Calculated for C14H21N3O5S3 : C, 41.26; H, 5.19 N, 10.31. Found: C, 41.35; H, 5.10; N, 10.28.

Workup

  1. temperaturemaintained at this temperature for 4 h
  2. customHalf of the reaction mixture was removed
  3. temperaturecooled on an ice bath
  4. additionmorpholine (3 mL) was added
  5. stirringwith stirring
  6. stirringThe reaction mixture was stirred for 18 h
  7. customevaporated to a residue which
  8. additionwas mixed with ethyl acetate (200 mL)
  9. washthis solution was washed with a saturated solution of sodium bicarbonate (100 mL)
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customevaporated to a residue which
  13. customwas purified by colunmn chromatography (silica, 4% methanol/methylene chloride)
  14. customto give a viscous oil which
  15. customcrystalized from methylene chloride/hexane

Sources & evidence

ORD record
ord-aed8b942ed98431a911432bd95fa03ec
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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