Potassium Hydroxide → 2-(3-Chloropropylthio)-5-nitrobenzenamine

HRID 50960

반응식

HRID 50960 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.[Cl:12][CH2:13][CH2:14][CH2:15][SH:16].[OH-].[K+]>COCCOC>[Cl:12][CH2:13][CH2:14][CH2:15][S:16][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[NH2:1]

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 677852-Fluoro-5-nitroanilineHCID 871343-Chloropropanethiol

생성물 1

HCID 227355412-(3-Chloropropylthio)-5-nitrobenzenamine수율 17%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

2-Amino-4-nitro-fluorbenzene (500 mg, 3.2 mmol), 3-chloro-1 propanethiol (354 mg, 3.2 mmol), and potassium hydroxide (269 mg, 4.8 mmol) were mixed together in ethylene glycol dimethyl ether (6.4 mL) and heated at reflux for 72 hours. The reaction was filtered and the filtercake washed with chloroform. The filtrate was concentrated and purified by flash column chromatography on 10 g if silica gel and eluted with 3% methanol in chloroform to give 2-[(3-chloropropyl)sulfanyl]-5-nitrophenylamine (130 mg, 17%). 1H NMR (CDCl3, 300 MHz): δ7.49-7.48 (m, 2H), 7.38 (dd, 1H, J=7.7 Hz, J=7.7 Hz), 4.55 (s-broad, 2H), 3.64 (t, 2H, J=6.2 Hz), 3.03 (t, 2H, J=7 Hz), 2.00 (q, 2H, J=7 Hz) ppm. Mass Spec (ESI):264 (base M+H).

후처리

  1. temperatureheated
  2. temperatureat reflux for 72 hours
  3. filtrationThe reaction was filtered
  4. washthe filtercake washed with chloroform
  5. concentrationThe filtrate was concentrated
  6. custompurified by flash column chromatography on 10 g if silica gel
  7. washeluted with 3% methanol in chloroform

출처 및 근거

ORD 기록
ord-27d01dcecd164d1e8069869a5cb0d0a0
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713471B1

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