Methyl Isocyanate → HCID 21399269, compound

HRID 1438854Notes

Reaction equation

HRID 1438854 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][CH3:9])[C:3]=1[C:10]#[N:11].[CH3:12][N:13]=[C:14]=[O:15]>C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC.O1CCCC1>[CH3:12][NH:13][C:14]([NH:1][C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][CH3:9])[C:3]=1[C:10]#[N:11])=[O:15]

Participants

5

Reactant 2

HCID 12228Methyl Isocyanate2×HCID 21399270HCID 21399270, compound

Product 1

HCID 21399269HCID 21399269, compound

Reagents, catalysts & solvents 2

HCID 9798523Di-n-butyl diacetoxy tinCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 35.0 g of 5-amino-4-cyano-3-(ethylthio)-isothiazole, 11.9 g of methyl isocyanate, 50 drops of dibutyltin diacetate in 175 ml of dried tetrahydrofuran was heated under reflux during 15 hours. Thin-layer chromatographic analysis of the reaction mixture indicated the reaction was 50% complete. An additional 11 ml of methyl isocyanate and 10-15 drops of dibutyltin diacetate were added. The reaction mixture was heated with stirring for 2 days. Thin-layer chromatographic analysis of the reaction mixture indicated the reaction to be complete. The reaction mixture was cooled, and the solid collected by filtration. The filtrate was evaporated to give a second crop, which was recrystallized from ethanol/dimethylformamide. The total yield of pure 1-methyl-3-(4-cyano-3-(ethylthio)-5-isothiazolyl)urea was 37.6 g; m.p. 246° (phase change) - 263°. The nmr spectrum was consistent with the assigned structure.

Workup

  1. temperatureunder reflux during 15 hours
  2. temperatureThe reaction mixture was heated
  3. customthe reaction
  4. temperatureThe reaction mixture was cooled
  5. filtrationthe solid collected by filtration
  6. customThe filtrate was evaporated
  7. customto give a second crop, which
  8. customwas recrystallized from ethanol/dimethylformamide
  9. custom263°

Sources & evidence

ORD record
ord-27c4c0f0eebb48a7bad2b29e5e314028
Source dataset
uspto-grants-1977_11
Patent number
US04057416

Reaction notes

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