Hydrochloric Acid → 3,5-Diacetylbenzenesulfonamide

HRID 2303590Notes

Reaction equation

HRID 2303590 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([C:11](=[O:13])[CH3:12])[CH:10]=1)N)(=[O:3])[CH3:2].Cl.[N+:15]([O-])([O-])=O.[Na+].[S:20](=[O:22])=[O:21]>C(O)(=O)C.O>[C:1]([C:4]1[CH:5]=[C:6]([S:20]([NH2:15])(=[O:22])=[O:21])[CH:8]=[C:9]([C:11](=[O:13])[CH3:12])[CH:10]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 24268Sodium NitrateHCID 463010Cni H1894

Product 1

HCID 184616083,5-Diacetylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

To a stirred solution of 3,5-diacetylaniline (3.00 grams) in a mixture of acetic acid (17 (mL) and hydrochloric acid (5.7mL) was added a solution of sodium nitrate (1.27 grams) in 2.1 mL of water. The solution was stirred for 20 minutes. 14 mL of acetic acid was saturated with sulfur dioxide gas, and this mixture was added to the reaction, followed by cuprous chloride (0.63 grams). Significant foaming occurred. The reaction mixture was stirred for one hour, diluted with water, and extracted with three portions of ethyl acetate. The combined ethyl acetate extracts were washed with water, and concentrated. The resulting oil was taken up in diethyl ether, and ammonia gas was bubbled through the solution. The resulting slurry was filtered, and the solid was taken up in acetone and filtered to remove ammonium chloride. Removal of the acetone in vacuo afforded 1.48 grams of the title compound, m.p. 179.2-180.7° C.

Workup

  1. additionthis mixture was added to the reaction
  2. stirringThe reaction mixture was stirred for one hour
  3. extractionextracted with three portions of ethyl acetate
  4. washThe combined ethyl acetate extracts were washed with water
  5. concentrationconcentrated
  6. customammonia gas was bubbled through the solution
  7. filtrationThe resulting slurry was filtered
  8. filtrationfiltered
  9. customto remove ammonium chloride
  10. customRemoval of the acetone in vacuo

Sources & evidence

ORD record
ord-210b5aa36fbe4b2e88c54efc1abe1b76
Source dataset
uspto-grants-2002_08
Patent number
US06433009B1

Reaction notes

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