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

HRID 1764837

반응식

HRID 1764837 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-91eb3af9f33c4c52933dcc80fdd64440
출처 데이터셋
uspto-grants-2007_06
특허 번호
USRE039679E1

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