Sulfur Dioxide → N,N-diethyl-1,2-benzenedisulfonamide

HRID 847655Notes

Reaction equation

HRID 847655 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])(=[O:10])=[O:9].[N:16]([O-])=O.[Na+].[S:20](=[O:22])=[O:21]>Cl.C(O)(=O)C.O>[CH2:12]([N:11]([CH2:14][CH3:15])[S:8]([C:3]1[C:2]([S:20]([NH2:16])(=[O:22])=[O:21])=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[O:10])=[O:9])[CH3:13]

Participants

7

Reactant 3

HCID 1119Sulfur DioxideHCID 128195982-Amino-N,N-diethylbenzenesulfonamideHCID 23668193Sodium Nitrite

Product 1

HCID 12819600N,N-diethyl-1,2-benzenedisulfonamide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 114 g of o-amino-N,N-diethylbenzenesulfonamide in a mixture of 400 ml of concentrated hydrochloric acid and 100 ml of glacial acetic acid was added a solution of 50 g of sodium nitrite in 130 ml of water at -5° to 0°. The solution was stirred at 0° for 15 minutes then poured into a mixture of 14 g of cuprous chloride and 100 ml of liquid sulfur dioxide in 550 ml of glacial acetic acid at 0°-5°. This mixture was stirred at 0° for 15 minutes then at room temperature for 3 hours before pouring into three liters of ice water. The crude suflonyl chloride was filtered off and washed with water. It was then dissolved in 1 l of ethyl ether, washed with water and dried over magnesium sulfate. To this ether solution was added 20 ml of liquid anhydrous ammonia at 5°-15°. After stirring overnight at room temperature the solid was filtered off, washed with water, ethanol and then 1-chlorobutane, Oven drying at 60° gave 91.8 g N,N-diethyl-1,2-benzenedisulfonamide, m.p. 156°-9°.

Workup

  1. stirringThis mixture was stirred at 0° for 15 minutes
  2. filtrationThe crude suflonyl chloride was filtered off
  3. washwashed with water
  4. dissolutionIt was then dissolved in 1 l of ethyl ether
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. additionTo this ether solution was added 20 ml of liquid anhydrous ammonia at 5°-15°
  8. stirringAfter stirring overnight at room temperature the solid
  9. filtrationwas filtered off
  10. washwashed with water, ethanol
  11. dry with material1-chlorobutane, Oven drying at 60°

Sources & evidence

ORD record
ord-cc94667f213640f396778d60d2b6e463
Source dataset
uspto-grants-1981_10
Patent number
US04293330

Reaction notes

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