3-Mercaptopropionic Acid → Cgp 20376
Reaction equation
[C:1]([C:5]1[S:6][C:7]2[CH:13]=[C:12]([N:14]=[C:15]=[S:16])[C:11]([O:17][CH3:18])=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[SH:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23]>CN(C)C=O>[C:22]([CH2:21][CH2:20][S:19][C:15](=[S:16])[NH:14][C:12]1[C:11]([O:17][CH3:18])=[CH:10][C:8]2[N:9]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[S:6][C:7]=2[CH:13]=1)([OH:24])=[O:23]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
27.8 g (0.10 mole) of 2-tert.-butyl-6-isothiocyano-5-methoxy-benzthiazole are dissolved in 150 ml of dimethylformamide and 14 g (0.13 mole) of 3-mercaptopropionic acid are added. The solution is stirred at room temperature under nitrogen for 2 hours, then poured onto 2 kg of ice and stirred until the product has become solid. It is filtered off, washed with water and heated in 700 ml of toluene, decanted from water, dried over sodium sulphate, clarified with active carbon and filtered. The filtrate is diluted at 30-40° with approximately 700 ml of petroleum ether and cooled slowly to 5°, filtered off and subsequently washed with petroleum ether. N-[2-tert.-butyl-5-methoxy-benzthiazol-6-yl]-dithiocarbamic acid S-(2-carboxyethyl)-ester having a melting point of 154-156° is obtained: ##STR14##