Methyl Isocyanate → N-[4-(6-chlorobenzothiazol-2-ylthio)phenyl]-N'-methylurea

HRID 64948Notes

Reaction equation

HRID 64948 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[Cl:5][C:6]1[CH:22]=[CH:21][C:9]2[N:10]=[C:11]([S:13][C:14]3[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=3)[S:12][C:8]=2[CH:7]=1>N1C=CC=CC=1>[Cl:5][C:6]1[CH:22]=[CH:21][C:9]2[N:10]=[C:11]([S:13][C:14]3[CH:20]=[CH:19][C:17]([NH:18][C:3]([NH:2][CH3:1])=[O:4])=[CH:16][CH:15]=3)[S:12][C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 202361324-(6-Chlorobenzothiazol-2-ylthio)-aniline

Product 1

HCID 20236131N-[4-(6-chlorobenzothiazol-2-ylthio)phenyl]-N'-methylureaYield 62.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl isocyanate (0.41 g) was added to a solution of 4-(6-chlorobenzothiazol-2-ylthio)-aniline (2.0 g) in pyridine (20 ml), with stirring. The mixture was stirred at room temperature for 12 hours and evaporated to dryness. The residue was dissolved in a minimal volume of boiling ethanol and the solution was cooled in a refrigerator. The resulting solid substance was collected by filtration and dried to give N-[4-(6-chlorobenzothiazol-2-ylthio)phenyl]-N'-methylurea (1.5 g), which had a melting point of 289°-291° C. This urea (1.4 g) was dissolved in 1,4-dioxane (50 ml), and chlorocarbonyl isocyanate (0.47 g) was added. The mixture was heated at the boiling point for 5 hours and evaporated to dryness. The solid residue was dissolved in a minimal volume of boiling ethanol and the solution was cooled in a refrigerator. The resulting solid substance was collected by filtration and dried to give 1.3 g of 1-[4-(6-chlorobenzothiazol-2-y(thio)phenyl]-3-methyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione of melting point 232°-233° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in a minimal volume of boiling ethanol
  4. temperaturethe solution was cooled in a refrigerator
  5. filtrationThe resulting solid substance was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-937040b10c254ca7a4087c4e60563540
Source dataset
uspto-grants-1986_09
Patent number
US04611060

Reaction notes

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