[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[C:7]([OH:9])=O.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:25]([NH2:33])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl.CN(C)C1C=CN=CC=1>[CH2:25]([NH:33][C:7]([C:6]1[S:5][N:4]=[N:3][C:2]=1[CH3:1])=[O:9])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1
A suspension of 9.65 g of 4-methyl-[1,2,3]thiadiazol-5-carboxylic acid in 70 ml of dichlormethane was cooled to 5° C. while stirring, treated with 0.15 g of 4-dimethylamino-pyridine and subsequently with 13.8 g of N,N'-dicyclohexyl-carbodiimide at such a rate that the internal temperature <10° C. could be maintained. After completion of the addition, the mixture was cooled to 5° C. and 8.92 g of phenethylamine were added at such a rate that the internal temperature of <37° C. could be maintained. After completion of the addition, the mixture was stirred for a further 1 h., then the precipitate was filtered off under suction, rinsed well with dichloromethane and the filtrate was evaporated. The residual yellow oil was subjected to chromatography on silica gel with hexane/ethyl acetate 50:50. There were obtained 15.66 g (92%) of 4-methyl-[1,2,3]thiadiazole-5-carboxylic acid phenethylamide as a colorless crystallizate of m.p. 64°-68° C. Recrystallization of a sample from tert.-butyl methyl ether gave colorless crystals of m.p. 64.5°-66° C.
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