5-(N,N-Dimethylaminosulfonyl)-1,3,4-thiadiazol-2-yl isocyanate → N-[5-(N,N-dimethylaminosulfonyl)-1,3,4-thiadiazol-2-yl]-N'-[2,2-dimethyl-2-(4-methyl-1,3-dioxolan-2-yl)ethyl]-N'-methylurea

HRID 127136Notes

Reaction equation

HRID 127136 reaction equation
[CH3:1][N:2]([CH3:14])[S:3]([C:6]1[S:10][C:9]([N:11]=[C:12]=[O:13])=[N:8][N:7]=1)(=[O:5])=[O:4].[CH3:15][C:16]([CH3:26])([CH:20]1[O:24][CH:23]([CH3:25])[CH2:22][O:21]1)[CH2:17][NH:18][CH3:19]>C(OCC)(=O)C>[CH3:1][N:2]([CH3:14])[S:3]([C:6]1[S:10][C:9]([NH:11][C:12]([N:18]([CH2:17][C:16]([CH3:15])([CH3:26])[CH:20]2[O:24][CH:23]([CH3:25])[CH2:22][O:21]2)[CH3:19])=[O:13])=[N:8][N:7]=1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 128944545-(N,N-Dimethylaminosulfonyl)-1,3,4-thiadiazol-2-yl isocyanateHCID 12894459HCID 12894459, compound

Product 1

HCID 20286111N-[5-(N,N-dimethylaminosulfonyl)-1,3,4-thiadiazol-2-yl]-N'-[2,2-dimethyl-2-(4-methyl-1,3-dioxolan-2-yl)ethyl]-N'-methylurea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-(N,N-Dimethylaminosulfonyl)-1,3,4-thiadiazol-2-yl isocynate dimer (6 grams) N-[2,2-dimethyl-2-(4-methyl-1,3-dioxolan-2-yl)ethyl]methylamine (6 grams) and ethyl acetate (20 ml) are charged into a glass reaction vessel fitted with a mechanical stirrer. The reaction mixture is heated on a steam bath for a period of about 2 hours. Solvent is then stripped off using a rotary evaporator to yield the desired product N-[5-(N,N-dimethylaminosulfonyl)-1,3,4-thiadiazol-2-yl]-N'-[2,2-dimethyl-2-(4-methyl-1,3-dioxolan-2-yl)ethyl]-N'-methylurea as the residue.

Workup

  1. customfitted with a mechanical stirrer
  2. temperatureThe reaction mixture is heated on a steam bath for a period of about 2 hours
  3. customa rotary evaporator

Sources & evidence

ORD record
ord-d9b8ab1e02d04c9aa147017dd487e343
Source dataset
uspto-grants-1981_03
Patent number
US04255182

Reaction notes

Loading…