4-Toluenesulfonyl chloride → HCID 10806320, compound

HRID 343354Notes

Reaction equation

HRID 343354 reaction equation
C(N(CC)CC)C.Cl.[OH:9][CH2:10][C:11]1[N:12]=[CH:13][NH:14][CH:15]=1.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:14]2[CH:15]=[C:11]([CH2:10][O:9][S:28]([CH3:27])(=[O:30])=[O:29])[N:12]=[CH:13]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chlorideHCID 178418488HCID 178418488, compound

Product 1

HCID 10806320HCID 10806320, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Triethylamine (25.9 ml) was added dropwise to a suspension of 4-hydroxymethylimidazole hydrochloride (10.0 g, 74 mmol) in dichloromethane (200 ml) containing 4-methylbenzenesulfonyl chloride (15.6 g) and the mixture stirred overnight before being washed with water and brine, dried (MgSO4), and evaporated to leave a colourless oil. This was chromatographed on silica gel, eluting with ethyl acetate/hexanes to give an oil which solidified on standing (15.0 g). A portion of this solid (1.0 g, 4 mmol) was dissolved in dichloromethane (15 ml), and the solution cooled in an ice bath as triethylamine (0.5 g), followed by methanesulfonyl chloride (0.55 g) in dichloromethane (1 ml) were added dropwise. After tlc indicated reaction to have completed, the mixture was washed with water and brine, then dried (MgSO4), before evaporating to leave the product as a white powder (1.3 g).

Workup

  1. washbefore being washed with water and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customto leave a colourless oil
  5. customThis was chromatographed on silica gel
  6. washeluting with ethyl acetate/hexanes
  7. customto give an oil which
  8. additionwere added dropwise
  9. customreaction
  10. washthe mixture was washed with water and brine
  11. dry with materialdried (MgSO4)
  12. custombefore evaporating

Sources & evidence

ORD record
ord-eafbe1c63169418cb98336b43229f4a8
Source dataset
uspto-grants-1999_01
Patent number
US05861407

Reaction notes

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