N,N'-Dimethylurea → HCID 21498416, compound

HRID 1729944Notes

Reaction equation

HRID 1729944 reaction equation
CNC1[S:4][C:5]([S:8](=[O:18])(=[O:17])[N:9]([CH3:16])[CH2:10][C:11]2[O:15][CH:14]=[CH:13][CH:12]=2)=[N:6][N:7]=1.[CH3:19]N=C=O.[CH3:23][NH:24][C:25]([NH:27][CH3:28])=[O:26]>C1(C)C=CC=CC=1>[CH2:10]([N:9]([CH3:16])[S:8]([C:5]1[S:4][C:23]([N:24]([CH3:19])[C:25]([NH:27][CH3:28])=[O:26])=[N:7][N:6]=1)(=[O:18])=[O:17])[C:11]1[O:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7293N,N'-DimethylureaHCID 12228Methyl IsocyanateHCID 21498439HCID 21498439, compound

Product 1

HCID 21498416HCID 21498416, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3 g. of 2-methylamino-5-[N-methyl-N-furfurylsulfamoyl]-1,3,4-thiadiazole (from Preparation 3) in 50 ml. of toluene was added 1 g. of methyl isocyanate. The reaction mixture was heated at reflux for about 3 hours. The reaction product mixture was cooled and the solid which precipitated was filtered off. The solid weighed about 2.5 g. It was recrystallized from commercial absolute ethanol to give tan crystals weighing about 1 g., and having a melting point of about 131°-132° C. The product was identified by NMR spectrum and elemental analyses as 1-[5-N-furfuryl-N-methylsulfamoyl)-1,3,4-thiadiazol-2-yl]-1,3-dimethylurea.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for about 3 hours
  3. temperatureThe reaction product mixture was cooled
  4. customthe solid which precipitated
  5. filtrationwas filtered off
  6. customIt was recrystallized from commercial absolute ethanol
  7. customto give tan crystals

Sources & evidence

ORD record
ord-d8791c5686064cf08684c0e04e3b6f25
Source dataset
uspto-grants-1976_11
Patent number
US03990881

Reaction notes

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