Benzenesulfonyl chloride, 4-chloro-3-nitro- → 4-Chloro-3-nitrobenzenesulfonic acid-n-(1-methylpiperidin-4-yl)-n-methylamide

HRID 50235

반응식

HRID 50235 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][CH3:9])[CH2:4][CH2:3]1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]>N1C=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]([CH3:9])[S:17]([C:14]2[CH:15]=[CH:16][C:11]([Cl:10])=[C:12]([N+:21]([O-:23])=[O:22])[CH:13]=2)(=[O:18])=[O:19])[CH2:4][CH2:3]1

참가 물질

4

반응물 2

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 5663231-Methyl-4-(methylamino)piperidine

생성물 1

HCID 113714564-Chloro-3-nitrobenzenesulfonic acid-n-(1-methylpiperidin-4-yl)-n-methylamide

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 2.2 mL (15 mmol) of 1-methyl-4-methylaminopiperidine in 60 mL pyridine, 3.8 g (15 mmol) of 4-chloro-3-nitrobenzenesulfonic acid chloride were added, in batches, whilst cooling with ice. The mixture was then stirred for two hours with cooling, then evaporated to dryness, the residue was mixed with about 50 mL of water and made alkaline with concentrated ammonia whilst stirring vigorously. The crude product precipitated was suction filtered and purified by column chromatography (250 g silica gel, eluant: dichloromethane with 1.5% ethanol). Yield: 1.6 g (31% of theory), C13H18ClN3O4S (347.8); Rf value: 0.19 (silica gel; dichloromethane/ethanol=19:1).

후처리

  1. temperaturewhilst cooling with ice
  2. temperaturewith cooling
  3. customevaporated to dryness
  4. additionthe residue was mixed with about 50 mL of water
  5. stirringwhilst stirring vigorously
  6. customThe crude product precipitated
  7. filtrationfiltered
  8. custompurified by column chromatography (250 g silica gel, eluant: dichloromethane with 1.5% ethanol)

출처 및 근거

ORD 기록
ord-a4b92adeb6194e9899e79b37a3d3ec15
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710055B2

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