Org. Synth. 1948, 28, 82
DOI: 10.15227/orgsyn.028.0082
p-NITROPHENYL SULFIDE
[Sulfide, bis-(p-nitrophenyl)]
Submitted by Charles C. Price and Gardner W. Stacy.
Checked by Cliff S. Hamilton and Paul D. Berry.
1. Procedure
In a 1-l. round-bottomed flask equipped with a reflux condenser are placed 157.5 g. (1 mole) of p-chloronitrobenzene, 160 g. (1 mole) of potassium xanthate (Note 1), and 450 ml. of 95% ethanol. This reaction mixture is heated under reflux on a steam bath for 48 hours. The crystalline product, which deposits from solution during the course of the reaction, is collected by filtration, crushed into small particles in a mortar, and washed twice with hot ethanol and once with hot water. The yield of p-nitrophenyl sulfide melting at 158–160° is 105–113 g. (76–82%). This product is pure enough for most purposes. Recrystallization from glacial acetic acid (15 ml. per gram) raises the melting point to 160–161°.
2. Notes
1.
Potassium xanthate may be prepared in the following manner: With heating,
300 g. (5.36 moles) of potassium hydroxide is dissolved in
3 l. of absolute ethanol. The solution is then cooled in an
ice bath, and the temperature is kept below 10° while
carbon disulfide is added in portions with stirring until the solution is no longer alkaline; about
456 g. (360 ml., 5.95 moles) of carbon disulfide is required. The
potassium xanthate is collected by suction filtration and air-dried on large sheets of
filter paper; yield,
429–472 g. (
50–55%).
3. Discussion
p-Nitrophenyl sulfide has been prepared by the reaction between
p-chloronitrobenzene and
sodium sulfide.
1 This is not a practical means of preparation, however, because of the variety of substances formed.
2 The method described has been published.
3 A preparation of pure
p-nitrophenyl sulfide has been reported from
p-chloronitrobenzene and
sodium thiosulfate.
4
Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)
ethanol (64-17-5)
acetic acid (64-19-7)
sodium thiosulfate (7772-98-7)
potassium hydroxide (1310-58-3)
carbon disulfide (75-15-0)
sodium sulfide (1313-82-2)
p-chloronitrobenzene (100-00-5)
potassium xanthate
p-Nitrophenyl sulfide,
Sulfide, bis-(p-nitrophenyl) (1223-31-0)
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