Toluene → HCID 21498410, compound

HRID 1729945Notes

Reaction equation

HRID 1729945 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([S:8](=[O:19])(=[O:18])[N:9]([CH3:17])[CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:6][N:7]=1.C1(C)C=CC=CC=1.[CH3:27][N:28]=[C:29]=[O:30]>C(OCC)(=O)C>[CH3:1][N:2]([C:3]1[S:4][C:5]([S:8](=[O:19])(=[O:18])[N:9]([CH3:17])[CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:6][N:7]=1)[C:29]([NH:28][CH3:27])=[O:30]

Participants

5

Reactant 3

HCID 1140TolueneHCID 12228Methyl IsocyanateHCID 21498425HCID 21498425, compound

Product 1

HCID 21498410HCID 21498410, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5.7 g. of 2-methylamino-5-[N-methyl-N-(3-pyridylmethyl)sulfamoyl]-1,3,4-thiadiazole (from Preparation 4) in 100 ml. of toluene was added 3 g. of methyl isocyanate. The mixture was heated at reflux for about 5 hours. The mixture was cooled and concentrated in vacuo to yield a semisolid residue. A sample of the semisolid subjected to thin layer chromatography in ethyl acetate showed three spots. The semisolid was chromatographed on a silica gel column using ethyl acetate. The eluate corresponding to the second spot material was collected. The eluate was concentrated to dryness in vacuo, leaving a residue. The residue was recrystallized from ethyl acetate to yield white crystals having a melting point of about 169°-170° C., and weighing about 2.2 g. The product was identified by NMR spectrum and elemental analyses as 1,3-dimethyl-1-[5-[N-methyl-N-(3-pyridylmethylsulfamoyl]-1,3,4-thiadiazol-2-yl]urea.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for about 5 hours
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated in vacuo
  5. customto yield a semisolid residue
  6. customThe semisolid was chromatographed on a silica gel column
  7. customThe eluate corresponding to the second spot material was collected
  8. concentrationThe eluate was concentrated to dryness in vacuo
  9. customleaving a residue
  10. customThe residue was recrystallized from ethyl acetate
  11. customto yield white crystals

Sources & evidence

ORD record
ord-1cb45fd213124c77ae1a86ce6ecd183d
Source dataset
uspto-grants-1976_11
Patent number
US03990881

Reaction notes

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