Dicyclohexylcarbodiimide → Benzothiazol-2-ylthio succinic anhydride
Reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[S:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[CH:25]([CH2:29][C:30]([OH:32])=[O:31])[C:26](O)=[S:27]>C(COC)OC>[S:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[CH:25]1[CH2:29][C:30](=[O:31])[O:32][C:26]1=[S:27]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 6.18 parts of dicyclohexylcarbodiimide in 30 parts by volume of dimethoxyethane is added dropwise, over 1.5 hours, to a stirred solution of 8.49 parts of benzothiazol-2-ylthio succinic acid prepared as in Example 1A in dimethoxyethane (70 parts by volume). The reaction is exothermic and the temperature is maintained at 25°-27° with cooling. When the addition is complete, stirring is continued for a further 1.5 hours and the precipitated dicyclohexylurea is removed by filtration. The filtrate is evaporated in vacuo and the residual solid is recrystallised from a mixture of dichloromethane and cyclohexane to give benzothiazol-2-ylthio succinic anhydride m.p. 129°-129° (with decomposition).