Hydrochloric Acid → 4-Sulfamoylbenzene-1-sulfonyl chloride

HRID 1173096Notes

Reaction equation

HRID 1173096 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[ClH:12].N([O-])=O.[Na+].[S:17](=[O:19])=[O:18]>C(O)(=O)C.O>[S:8]([C:5]1[CH:6]=[CH:7][C:2]([S:17]([Cl:12])(=[O:19])=[O:18])=[CH:3][CH:4]=1)(=[O:10])(=[O:9])[NH2:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 5333SulfanilamideHCID 23668193Sodium Nitrite

Product 1

HCID 109561594-Sulfamoylbenzene-1-sulfonyl chloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

6.4 g (37.2 mmol) of 4-aminobenzenesulfonamide was added to a mixed solution of 12.5 ml of water and 6.3 ml of concentrated hydrochloric acid, followed by stirring. An aqueous saturated solution containing 2.56 g (37.1 mmol) of sodium nitrite was added drop wise there into at 0° C. or less. The reaction solution was added to an acetic acid solution saturated with sulfur dioxide (solution obtained by saturating 35 ml of acetic acid with sulfur dioxide and then adding 1.5 g of cupric chloride dihydrate thereto) under ice-cooling with stirring. After 10 minutes, the reaction solution was poured into ice-water, and the precipitates were collected by filtration and washed with water. The precipitates were dissolved in tetrahydrofuran, dried over magnesium sulfate and then concentrated to dryness, to give 3.5 g of the title compound.

Workup

  1. additionwas added drop wise there into at 0° C. or less
  2. customobtained
  3. concentrationby saturating 35 ml of acetic acid with sulfur dioxide
  4. additionadding 1.5 g of cupric chloride dihydrate
  5. temperature) under ice-cooling
  6. stirringwith stirring
  7. additionthe reaction solution was poured into ice-water
  8. filtrationthe precipitates were collected by filtration
  9. washwashed with water
  10. dissolutionThe precipitates were dissolved in tetrahydrofuran
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-efc3eaf48c6146a29369b96165620cd7
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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