Triethylamine → 2-(Dimethylaminosulfonyloxy)benzenesulfonamide

HRID 462335Notes

Reaction equation

HRID 462335 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].C(N(CC)CC)C.[CH3:19][N:20]([CH3:25])[S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[CH3:19][N:20]([CH3:25])[S:21]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:9])=[O:10])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 6375462-Hydroxybenzene-1-sulfonamide

Product 1

HCID 134731262-(Dimethylaminosulfonyloxy)benzenesulfonamideYield 54.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To 6.8 g (0.04 mole) 2-hydroxybenzenesulfonamide in 100 ml methylene chloride was added 4.4 g (0.044 mole) triethylamine and 6.3 g (0.044 mole) dimethylsulfamoyl chloride in 5 ml methylene chloride, keeping the reaction temperature <10° C. The mixture was then warmed to room temperature and stirred 72 hours. The reaction mixture was then diluted with 100 ml methylene chloride washed with 100 ml water, 100 ml 1% HCl and dried over MgSO4. The solvent was evaporated to give a crude yellow oil that slowly solidified on standing. The solids were then triturated with hexanes and filtered to give 6.1 g of a tan solid, m.p. 88°-89° C.

Workup

  1. customthe reaction temperature <10° C
  2. washwashed with 100 ml water, 100 ml 1% HCl
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated
  5. customto give a crude yellow oil that
  6. customThe solids were then triturated with hexanes
  7. filtrationfiltered

Sources & evidence

ORD record
ord-7a4f7fd8b0564b538ff8cbe360483b86
Source dataset
uspto-grants-1985_05
Patent number
US04515624

Reaction notes

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