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

HRID 2205895노트

반응식

HRID 2205895 반응식
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]

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c90dd80dc026452f9ebb3a097b4d8a72
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371319B2

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