Hydrochloric Acid → Benzenesulfonamide, 4-amino-3-chloro-N,N-dimethyl-

HRID 2205895Notes

Reaction equation

HRID 2205895 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][C:6]=1[Cl:15])(=O)C.[CH3:16][NH:17][CH3:18].Cl.CO>>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:17]([CH3:18])[CH3:16])(=[O:13])=[O:12])=[CH:7][C:6]=1[Cl:15]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 887MethanolHCID 2827493-Chloro-4-acetamidobenzene-1-sulfonyl chloride

Product 1

HCID 205923Benzenesulfonamide, 4-amino-3-chloro-N,N-dimethyl-Yield 16%

Procedure

A suspension of 4-acetamido-3-chlorobenzene-1-sulfonyl chloride (0.96 g, 3.58 mmol) in a dimethylamine solution (2M in MeOH, 5.37 mL, 10.7 mmol) was stirred at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure and the residue was then redissolved in MeOH (17.9 mL). A 1M HCl solution in MeOH (5.37 mL, 5.37 mmol) was added and the reaction mixture was refluxed for 6 hours before being concentrated under reduced pressure. The residue was purified via Biotage silica gel column chromatography eluting with (cyclohexane/EtOAc 80/20 to 60/40) to afford the title product as a white solid (133 mg, 16%). 1H NMR (500 MHz, CDCl3) d 2.70 (s, 6H), 4.54 (br s, 2H), 6.83 (d, J=8.5 Hz, 1H), 7.48 (dd, J=8.5, 2.1 Hz, 1H), 7.70 (d, J=2.1 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was then redissolved in MeOH (17.9 mL)
  3. temperaturethe reaction mixture was refluxed for 6 hours
  4. concentrationbefore being concentrated under reduced pressure
  5. customThe residue was purified via Biotage silica gel column chromatography
  6. washeluting with (cyclohexane/EtOAc 80/20 to 60/40)

Sources & evidence

ORD record
ord-c90dd80dc026452f9ebb3a097b4d8a72
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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