2246
Russ.Chem.Bull., Int.Ed., Vol. 56, No. 11, November, 2007
Vaganova et al.
volume and a solution of 18ꢀcrownꢀ6 (1.0 g, 4 mmol) in MTBE
(6 mL) was added. The precipitate (1.4 g) was filtered off and
combined with the precipitate obtained previously. The filtrate
was washed with water (4×15 mL), the organic layer was sepaꢀ
rated and dried over anhydrous MgSO4, and MTBE was distilled
off. From the filtrate, phenylenediamine 9c was isolated (2.9 g,
66% in relation to the content in the initial mixture), purity 97%,
m.p. 132—134 °C (cf. Ref. 24: m.p. 127—128 °C; cf. Ref. 3e:
m.p. 132—132.5 °C).
The combined precipitates of the complexes (3.5 g) were
shaken with a mixture of MTBE (30 mL) and water (30 mL).
The organic layer was washed with water (4×15 mL) and dried
over MgSO4, and MTBE was distilled off to give a mixture of
diamines 9c and 9d (1.4 g, 8 mmol) in 3 : 7 ratio. A solution of
18ꢀcrownꢀ6 (0.7 g, 3.5 mmol) in MTBE (3 mL) was added to a
solution of this mixture in MTBE (5 mL) to give the complex of
individual phenylenediamine 9d and 18ꢀcrownꢀ6 (1.3 g), which
was decomposed as described above to give phenylenediamine
9d (0.5 g, 67% in relation to the content in the initial mixture),
purity 99%, m.p. 145—146 °C (cf. Ref. 6: m.p. 142—144 °C).
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Received February 9, 2007;
in revised form June 1, 2007