1,3-Dioxolane-2-methanamine, N-methyl- → N-[5-(N,N-dimethylaminosulfonyl)-1,3,4-thiadiazol-2-yl]-N'-(1,3-dioxolan-2-ylmethyl)-N'-methylurea

HRID 127129Notes

Reaction equation

HRID 127129 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].[O:15]1[CH2:19][CH2:18][O:17][CH:16]1[CH2:20][NH:21][CH3:22]>C(OCC)(=O)C>[CH3:1][N:2]([CH3:14])[S:3]([C:6]1[S:10][C:9]([NH:11][C:12]([N:21]([CH2:20][CH:16]2[O:17][CH2:18][CH2:19][O:15]2)[CH3:22])=[O:13])=[N:8][N:7]=1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 5417541,3-Dioxolane-2-methanamine, N-methyl-HCID 128944545-(N,N-Dimethylaminosulfonyl)-1,3,4-thiadiazol-2-yl isocyanate

Product 1

HCID 12894461N-[5-(N,N-dimethylaminosulfonyl)-1,3,4-thiadiazol-2-yl]-N'-(1,3-dioxolan-2-ylmethyl)-N'-methylurea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-(N,N-Dimethylaminosulfonyl)-1,3,4-thiadiazol-2-yl isocyanate dimer (6 grams), N-(1,3-dioxolan-2-ylmethyl)-N-methylamine (6 grams) and ethyl acetate (20 ml) were charged into a glass reaction vessel fitted with a mechanical stirrer. The reaction mixture was heated on a steam bath for a period of about 2 hours. Solvent was then stripped off using a rotary evaporator to yield the desired product N-[5-(N,N-dimethylaminosulfonyl)-1,3,4-thiadiazol-2-yl]-N'-(1,3-dioxolan-2-ylmethyl)-N'-methylurea as the residue. Melting point 100°-110° C.

Workup

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

Sources & evidence

ORD record
ord-7a6eb0a19767460d820ab947b30a4bad
Source dataset
uspto-grants-1981_03
Patent number
US04255182

Reaction notes

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