1.HCI ( 2 g) treat,ed as above gave 33.AcOH (0.23 g), mmp l l l " , and 33 (0.6 g), mmp 106", by fractional crystallization. The mother liquors were separated chemically to give a nonbasic part which yielded 45 (0.6 g), mmp 85' from EtOAc-petroleum ether.b.-AcC1 (1.57 g, 1 equiv) in CaHjN (10 ml) was added to 33 (4.58 g) in CZHSN (25 ml) at 0". After 18 hr E t 2 0 (100 ml) was added and t'he solution n-as washed with 2 S HC1. The Et20 solut,ion gave a gum containing ester impurity (ir). MeOH (90 ml) and SaOII (lo%, 5.8 ml) were added. After 2.5 hr the LleOH was evaporated in vacuo, Et20 was added, and the Et& solution was washed with 2 iV HC1. The Et?O sollition gave 45, mp 86-87" from EtOAc-petroleum ether (bp 40-60'). Anal. (CnHII-S-[2-Isopropylamino-l-( 2-naphthyl )ethyl] isothiourea .2HC1(12).-Compo~ind 1 (4 g) and thiourea (1.1 g) in EtOH (150 ml) were heated under reflux for 9 hr and tben the EtOH was evaporated to give 12.2-Isopropylamino-l-( 2-naphthy1)ethanethiol ( 13).-Compound 12 (3.8 g), 1 IT NaOH (63 ml), and MeOH (200 ml) were heated ririder reflm for 4 hr and then the XeOH was evaporated. Et,,O extraction gave 13, converted into its HCl by Et,20-HCl: iimr 7 2.15-2.80 (multiplet, ArH , 7 ) , 6.25 (X part of ABX, SCH<, l ) , 7.85-7.97 (multiplet, AB part of ABX, CHzS, 2 ) , 7.20-7.60 (septet, i-Pr CH, l), 8.72 (singlet, T1" and SH, 2 ) , 9.08 and 9.13
