[OH:1][C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][S:5][C:4](=[S:7])[N:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[BH4-].[K+]>CO.O.C1CCCCC1.C(OCC)(=O)C>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[NH:3][C:4](=[S:7])[S:5][CH2:6][CH:2]([OH:1])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1The procedure of Example 3 is followed, but a suspension of 4-hydroxy-4-phenyl-3-(pyrid-2-yl)-thiazolidine-2-thione (23.0 g) in methanol (240 cc) and a solution of potassium borohydride (4.3 g) in distilled water (60 cc) are used as the starting materials at a maximum of 35° C. The reaction is allowed to proceed for 30 minutes at 25°-35° C. The crude product (26.1 g) is dissolved in a mixture of cyclohexane (200 cc) and ethyl acetate (50 cc). The solution is chromatographed on silica (0.2-0.5 mm) (280 g) contained in a column of diameter 4 cm. Elution is carried out with a mixture of cyclohexane (480 cc) and ethyl acetate (120 cc) and then with a mixture of cyclohexane (280 cc) and ethyl acetate (120 cc), these eluates being discarded. Elution is continued with a mixture of cyclohexane (700 cc) and ethyl acetate (300 cc), this eluate being collected and evaporated to dryness under reduced pressure (20 mm Hg) at 45° C. The chromatographed product (18.1 g) is purified by recrystallisation from a mixture of ethyl ether (90 cc) and petroleum ether (b.p. 40° to 65° C., 30 cc). 2-Hydroxy-2-phenylethyl pyrid-2-yldithiocarbamate (14.9 g), which melts at 82° C., is obtained.
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