Sulfur Dioxide → HCID 13178728, compound

HRID 434460Notes

Reaction equation

HRID 434460 reaction equation
[CH3:1][N:2]([CH3:14])[S:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1N)(=[O:5])=[O:4].[N:15]([O-])=O.[Na+].[S:19](=[O:21])=[O:20]>Cl.C(O)(=O)C.O>[CH3:1][N:2]([CH3:14])[S:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:19]([NH2:15])(=[O:21])=[O:20])(=[O:5])=[O:4]

Participants

7

Reactant 3

HCID 1119Sulfur DioxideHCID 13178727HCID 13178727, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13178728HCID 13178728, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 53.5 g of the product of Example 3 in a mixture of 225 ml of concentrated hydrochloric acid and 75 ml of glacial acetic acid was added a solution of 21.4 g of sodium nitrite in 70 ml of water at -5° to 0°. The solution was stirred at 0° for 15 minutes, then poured into a mixture of 6 g of cuprous chloride, 48 ml of liquid sulfur dioxide in 300 ml of glacial acetic acid at 0°-4°. This mixture was stirred at 0° for 1 hour, then at 25° for 2 hours before being poured into 2 liters of ice-water. The precipitate was filtered and washed with water then suspended in 250 ml of ether and treated with 11.0 ml of liquid anhydrous ammonia at 5°-15°. After stirring at 25° for 30 minutes the precipitate was filtered off and washed well with ether then water. Oven drying at 60° gave 40.2 g of 2-[(dimethylamino)sulfonylmethyl]benzenesulfonamide, m.p. 145°-150°.

Workup

  1. stirringThis mixture was stirred at 0° for 1 hour
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. additiontreated with 11.0 ml of liquid anhydrous ammonia at 5°-15°
  5. stirringAfter stirring at 25° for 30 minutes the precipitate
  6. filtrationwas filtered off
  7. washwashed well with ether
  8. customOven drying at 60°

Sources & evidence

ORD record
ord-224616d07d0c4738a4087549ac78a649
Source dataset
uspto-grants-1983_08
Patent number
US04397679

Reaction notes

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