Reaction #79238

Reaction equation

2-Amino-4-nitro-fluorbenzene

3-chloro-1 propanethiol

potassium hydroxide

→

2-[(3-chloropropyl)sulfanyl]-5-nitrophenylamine

Yield 17.0%

Solvents

ethylene glycol dimethyl ether

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureat reflux for 72 hours
3. 3
   FiltrationThe reaction was filtered
4. 4
   Washthe filtercake washed with chloroform
5. 5
   ConcentrationThe filtrate was concentrated
6. 6
   Otherpurified by flash column chromatography on 10 g if silica gel
7. 7
   Washeluted with 3% methanol in chloroform

Procedure

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).

Source