5-(N,N-Dimethylaminosulfonyl)-1,3,4-thiadiazol-2-yl isocyanate → N-[5-(N,N-dimethylaminosulfonyl)-1,3,4-thiadiazol-2-yl]-N'-(4-methyl-1,3-dioxan-2-ylmethyl)-N'-methylurea
Reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][O:5][CH:4]([CH2:8][NH:9][CH3:10])[O:3]1.[CH3:11][N:12]([CH3:24])[S:13]([C:16]1[S:20][C:19]([N:21]=[C:22]=[O:23])=[N:18][N:17]=1)(=[O:15])=[O:14]>C(Cl)(Cl)Cl>[CH3:11][N:12]([CH3:24])[S:13]([C:16]1[S:20][C:19]([NH:21][C:22]([N:9]([CH2:8][CH:4]2[O:3][CH:2]([CH3:1])[CH2:7][CH2:6][O:5]2)[CH3:10])=[O:23])=[N:18][N:17]=1)(=[O:15])=[O:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
N-(4-methyl-1,3-dioxan-2-ylmethyl)-methylamine (6 grams), 5-(N,N-dimethylaminosulfonyl)-1,3,4-thiadiazol-2-yl isocyanate dimer (6 grams) and chloroform (20 ml) were charged into a glass reaction vessel and stirred at room temperature for a period of about 2 hours. The solvent was then stripped off on a rotary evaporator and the residue treated with a mixture of diethyl ethyl (100 ml)/water (50 ml). The ether, layer was isolated and dried. Ether was stripped off an a rotary evaporator to yield the desired product N-[5-(N,N-dimethylaminosulfonyl)-1,3,4-thiadiazol-2-yl]-N'-(4-methyl-1,3-dioxan-2-ylmethyl)-N'-methylurea as the residue. Melting point 131° C.-133° C.
Workup
- customThe solvent was then stripped off on a rotary evaporator
- additionthe residue treated with a mixture of diethyl ethyl (100 ml)/water (50 ml)
- customThe ether, layer was isolated
- customdried
- customa rotary evaporator
Sources & evidence
- ORD record
- ord-15b17a35a53c4cf5a23c830ab5c52269
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04255182
Reaction notes
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