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

HRID 2205895ノート

反応式

HRID 2205895 の反応式
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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c90dd80dc026452f9ebb3a097b4d8a72
出典データセット
uspto-grants-2016_06
特許番号
US09371319B2

反応ノート

読み込み中…