Ammonia → 4-bromo-3-methylbenzenesulfonamide

HRID 1754937Notes

Reaction equation

HRID 1754937 reaction equation
[NH3:1].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][C:4]=1[CH3:13]>C1COCC1>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH2:1])(=[O:11])=[O:10])=[CH:5][C:4]=1[CH3:13]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 27375034-Bromo-3-methylbenzene-1-sulfonyl chloride

Product 1

HCID 27374094-bromo-3-methylbenzenesulfonamideYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 28% aqueous NH3 solution (2.0 ml) was added to a solution of 4-bromo-3-methyl-benzenesulfonyl chloride (250 mg, 0.927 mmol) in THF (2.0 ml) at 0° C. The mixture was stirred at 0° C. for 6.5 hours. The reaction mixture was quenched with 1 N HCl and extracted with CH2Cl2. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (CH2Cl2—AcOEt) to give 4-bromo-3-methyl-benzenesulfonamide as a white powder (126 mg, 54%).

Workup

  1. customThe reaction mixture was quenched with 1 N HCl
  2. extractionextracted with CH2Cl2
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (CH2Cl2—AcOEt)

Sources & evidence

ORD record
ord-330655da7aef47a4b967a7926a622a5a
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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