Methyl Isocyanate → HCID 20136106, compound

HRID 579703Notes

Reaction equation

HRID 579703 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N:10]2[CH:14]([OH:15])[CH2:13][N:12]([CH3:16])[C:11]2=[O:17])=[C:4]([F:18])[CH:3]=1.[CH3:19][N:20]=[C:21]=[O:22]>C(#N)C.N12CCC(CC1)CN2>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N:10]2[CH:14]([O:15][C:21](=[O:22])[NH:20][CH3:19])[CH2:13][N:12]([CH3:16])[C:11]2=[O:17])=[C:4]([F:18])[CH:3]=1

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 20136105HCID 20136105, compound

Product 1

HCID 20136106HCID 20136106, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 136165Diazabicyclo(2.2.2)octaneCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

27.5 g (0.10 mol) of 3-(4-chloro-2-fluoro-5-methoxyphenyl)-4-hydroxy-1-methylimidazolidin-2-one (Example 1) are dissolved in 200 ml of acetonitrile, 50 mg of diazabicyclo[2.2.2]octane are added, and 6.84 g (0.12 mol) of methyl isocyanate are added dropwise at 20° C. The mixture is stirred for 5 hours at 50° C. and the solvent is removed by distillation. The solid residue which remains is boiled up in 200 ml of ether and cooled in an ice-bath. The precipitate is filtered off under suction and dried. 31.0 g (93% of theory) of 3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-methyl-4-(N-methylcarbamoyloxy)imidazolidin2-one are obtained in the form of colorless crystals having the melting point 128°-131° C.

Workup

  1. customthe solvent is removed by distillation
  2. temperaturecooled in an ice-bath
  3. filtrationThe precipitate is filtered off under suction
  4. customdried

Sources & evidence

ORD record
ord-0eb699db8def4736890ea8ee6bfdbdc8
Source dataset
uspto-grants-1988_06
Patent number
US04749403

Reaction notes

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