[NH2:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]#[N:12])=[CH:8][C:7]([S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:6][CH:5]=2.[H-].[Na+].[C:22](=O)([O:26]C1C=CC=CC=1)[O:23][CH2:24][CH3:25].O>CN(C)C=O.C(O)(=O)C>[C:11]([C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:8]=2)[NH:3][C:2]=1[NH:1][C:22](=[O:26])[O:23][CH2:24][CH3:25])#[N:12]
To an ice-cooled solution of 2-amino-3-cyano-5-(phenylthio)indole (1.5 g., 5.7mM.) in dimethyl formamide (20 ml.) was added sodium hydride (0.27 g., 50% w/w dispersion in mineral oil, 5.7mM.) followed by ethyl phenyl carbonate (0.94 g., 5.7mM.). The mixture was stirred overnight and allowed to warm to room temperature. T.l.c. indicated the reaction was complete. The reaction mixture was poured into rapidly stirred water and neutralised with acetic acid. The cream-coloured precipitate was filtered off and dried to give the crude product (1.62 g.) m.p. 181°-2° C. Recrystallisation from ethanol gave colourless crystals of ethyl 3-cyano-5-(phenylthio)indol-2-ylcarbamate, m.p. 190.5°-191.5° C. (0.82 g., 43%). ##STR2##
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