Preparation
To a flask containing 7.9 gm (0.33 mole) of sodium hydride in 100 ml of tetrahydrofuran is slowly added a mixture of 9.3 gm (0.1 mole) of aniline and 25.3 gm (0.10 mole) of bromoform. After the addition, the reaction is stirred for 1-2 hr at room temperature, and water is added (100 ml) dropwise. Ether (200 ml) is added and the ether layer washed four times with 50-ml portions of water, three times with 20-ml portions of dilute hydrochloric acid, and then with water. The resulting ether layer is dried over sodium sulfate, concentrated, and the residue distilled to afford 4.7 gm (45%), b.p. 52-53°C (13 mm Hg).
References
1. For general reviews on isocyanide chemistry, see: (a) Isonitrile Chemistry; Ugi, I., Ed.; Academic: New York, 1971. (b) Periasamy, M. P.; Walborsky, H. M. OPP 1979, 11, 295.
2. For applications in heterocyclic synthesis, see: Marcaccini, S.; Torroba, T. OPP 1993, 25, 141.
3. (a) Grundmann, C. CB 1958, 91, 1380. (b) Ugi, I.; Meyr, R. OS 1961, 41, 101. (c) Obrecht, R.; Herrmann, R.; Ugi, I. S 1985, 400.
4. Figueroa-Villar, J. D.; Carnieiro, C. L.; Cruz, E. R. H 1992, 34, 891
