Methyl Isocyanate → HCID 54329983, compound

HRID 616514Notes

Reaction equation

HRID 616514 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([N:7]([CH2:9][CH3:10])[CH3:8])[C:3]=1[C:11]#[N:12].[CH3:13][N:14]=[C:15]=[O:16].C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC>O1CCCC1>[CH3:13][NH:14][C:15]([NH:1][C:2]1[S:6][N:5]=[C:4]([N:7]([CH2:9][CH3:10])[CH3:8])[C:3]=1[C:11]#[N:12])=[O:16]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 9798523Di-n-butyl diacetoxy tinHCID 53689667HCID 53689667, compound

Product 1

HCID 54329983HCID 54329983, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 11 g of 5-amino-4-cyano-3-(ethylmethylamino)isothiazole, 6.8 g of methyl isocyanate, 2 ml of dibutyltin diacetate, and 50 ml of tetrahydrofuran was heated under reflux overnight. After cooling, the solution was evaporated under reduced pressure. The residue was recrystallized from toluene to yield 9.8 g of 1-methyl-3-(4-cyano-3-(ethylmethylamino)-5-isothiazolyl)urea, mp 175°. The ir and nmr spectra were consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. customthe solution was evaporated under reduced pressure
  5. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-e482d81caa224c58bdd5f84a8bc64eee
Source dataset
uspto-grants-1978_02
Patent number
US04075001

Reaction notes

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