Sulfuric Acid → 4,N-Diacetyl-2-chloro-benzenesulfonamide

HRID 1098753Notes

Reaction equation

HRID 1098753 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[C:6]([Cl:14])[CH:5]=1)(=[O:3])[CH3:2].[C:15](OC(=O)C)(=[O:17])[CH3:16].S(=O)(=O)(O)O>C(#N)C.O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:15](=[O:17])[CH3:16])(=[O:12])=[O:11])=[C:6]([Cl:14])[CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 130229094-Acetyl-2-chlorobenzenesulfonamide

Product 1

HCID 595061464,N-Diacetyl-2-chloro-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of the product obtained in step 2 (0.40 mg, 1.71 mmol) in ACN (3 ml) was added acetic anhydride. Concentrated sulphuric acid (2.8 μl, 5 mg, 51 μM) was added at 60° C. and the reaction mixture was stirred for 40 min at that temperature. The cooled reaction mixture was diluted with water, extracted with dichloromethane, dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The desired product was obtained (yield: 460 mg, 97%) and used in the following step without further purification.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-63903f16f12f49aaac8d95089f011203
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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