Org. Synth. 1947, 27, 58
DOI: 10.15227/orgsyn.027.0058
1-METHYL-1-(1-NAPHTHYL)-2-THIOUREA
[Urea, 1-methyl-1-(1-naphthyl)-2-thio-]
Submitted by Homer W. J. Cressman
Checked by Nathan L. Drake and Werner R. Boehme.
1. Procedure
The apparatus, consisting of a
1-l. three-necked flask, fitted with a
glycerol-sealed mechanical stirrer, two inlet tubes (10-mm. bore) extending nearly to the blades of the stirrer, and an outlet tube
(Note 1), is set up in a good
hood. Into a solution of
91 g. (0.5 mole) of N-methyl-1-naphthylcyanamide (p. 608) in
350 ml. of absolute ethanol, mechanically stirred and cooled by immersion of the flask in a
water bath maintained at 20–25°,
ammonia is bubbled at a moderate rate. After 5 minutes,
hydrogen sulfide (Note 2) is passed into the solution at about the same rate. The introduction of
ammonia is continued for 1.5 hours;
hydrogen sulfide is passed into the mixture an additional 30 minutes. A white solid begins to separate soon after the first addition of
hydrogen sulfide. After the mixture is chilled in an
ice-salt bath, it is filtered. The solid is suspended in 350 ml. of cold water, again separated by filtration, and finally washed with two 100-ml. portions of water, then with two
100-ml. portions of methanol, and dried. The yield of
1-methyl-1-(1-naphthyl)-2-thiourea, m.p.
168–170° (Note 3), amounts to
89–97 g. (
82–90%); this material is suitable for most purposes.
2. Notes
1.
The use of an alkali
trap1 is recommended.
2.
This general reaction can be used for preparing other unsymmetrical thioureas when the desired cyanamides can be obtained. The submitter has also prepared
1-methyl-1-(1-naphthyl)-2-selenourea, m.p.
174–175° with decomposition, and
1-ethyl-1-(1-naphthyl)-2-selenourea, m.p.
168–170° with decomposition, by substitution of
hydrogen selenide for
hydrogen sulfide.
3.
The
thiourea can be further purified by recrystallization from
ethanol. The recrystallized product melts at
170–171°.
3. Discussion
The preparation of this compound is not reported in the literature.
This preparation is referenced from:
Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)
ethanol (64-17-5)
ammonia (7664-41-7)
methanol (67-56-1)
hydrogen sulfide (7783-06-4)
thiourea (62-56-6)
1-methyl-1-(1-naphthyl)-2-thiourea,
Urea, 1-methyl-1-(1-naphthyl)-2-thio- (53663-34-6)
N-Methyl-1-naphthylcyanamide (53663-33-5)
1-methyl-1-(1-naphthyl)-2-selenourea
1-ethyl-1-(1-naphthyl)-2-selenourea
hydrogen selenide (7782-49-2)
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