Methyl Isocyanate → 1-Methyl-3-(4-cyano-3-isopropoxy-5-isothiazolyl)urea

HRID 1439336Notes

Reaction equation

HRID 1439336 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([O:7][CH:8]([CH3:10])[CH3:9])[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]([O:7][CH:8]([CH3:10])[CH3:9])[C:3]=1[C:11]#[N:12])=[O:16]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 9798523Di-n-butyl diacetoxy tinHCID 213968055-Amino-4-cyano-3-isopropoxyisothiazole

Product 1

HCID 213968131-Methyl-3-(4-cyano-3-isopropoxy-5-isothiazolyl)ureaYield 74.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the manner of Example V D, a mixture of 11 g of 5-amino-4-cyano-3-isopropoxyisothiazole and 6.8 g of methyl isocyanate in 50 ml of dry tetrahydrofuran containing 2 ml of dibutyltin diacetate were allowed to react under reflux overnight. Volatile materials were removed under reduced pressure and the residue was recrystallized from ethyl acetate to yield 10.8 g of 1-methyl-3-(4-cyano-3-isopropoxy-5-isothiazolyl)urea, mp 238° (decomposes.) The ir and nmr spectra were consistent with the assigned structure.

Workup

  1. customto react
  2. temperatureunder reflux overnight
  3. customVolatile materials were removed under reduced pressure
  4. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-55f8b4f3db3a4e5381c2caf9be67f8db
Source dataset
uspto-grants-1977_11
Patent number
US04059433

Reaction notes

Loading…