Isocyanatocarbonyl chloride → HCID 13506383, compound

HRID 1589134Notes

Reaction equation

HRID 1589134 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]=[C:7]([S:9][C:10]3[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH:19][CH3:20])=[O:18])=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.Cl[C:24]([N:26]=[C:27]=[O:28])=[O:25]>O1CCOCC1>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]=[C:7]([S:9][C:10]3[CH:11]=[CH:12][C:13]([N:16]4[C:24](=[O:25])[NH:26][C:27](=[O:28])[N:19]([CH3:20])[C:17]4=[O:18])=[CH:14][CH:15]=3)[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 119708Isocyanatocarbonyl chlorideHCID 20236131N-[4-(6-chlorobenzothiazol-2-ylthio)phenyl]-N'-methylurea

Product 1

HCID 13506383HCID 13506383, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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-ylthio)phenyl]-3-methyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione of melting point 232°-233° C.

Workup

  1. temperatureThe mixture was heated at the boiling point for 5 hours
  2. customevaporated to dryness
  3. dissolutionThe solid 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-1cd8195710fe496f8ea2e51d2bf9d542
Source dataset
uspto-grants-1986_02
Patent number
US04568674

Reaction notes

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