Methyl Isocyanate → HCID 13921216, compound

HRID 580270Notes

Reaction equation

HRID 580270 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:17]([CH3:18])=[C:16]([NH2:19])[C:15]([CH3:20])=[N:14]1.[CH3:21][N:22]=[C:23]=[O:24]>O1CCCC1.C(N(CC)CC)C>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:17]([CH3:18])=[C:16]([NH:19][C:23]([NH:22][CH3:21])=[O:24])[C:15]([CH3:20])=[N:14]1

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 13921211HCID 13921211, compound

Product 1

HCID 13921216HCID 13921216, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(2-fluoro-4-chloro-5-isopropoxyphenyl)-3,5-dimethyl-4-aminopyrazole (29.8 g) in tetrahydrofuran (100 ml) was added one drop of triethylamine and then added dropwise a solution of methyl isocyanate (6.0 g) in tetrahydrofuran (50 ml). After the completion of addition, the reaction mixture was left to stand at room temperature for one hour. Removal of the solvent from the reaction solution by distillation in vacuo gave the titled compound (34.7 g) as a white crystalline solid. Recrystallization of the solid from a mixture of cyclohexane/acetone provided a white crystalline solid. m.p. 184°-185° C.

Workup

  1. additionAfter the completion of addition
  2. waitthe reaction mixture was left
  3. customRemoval of the solvent from the reaction solution
  4. distillationby distillation in vacuo

Sources & evidence

ORD record
ord-d4aa09f3bf2641498d79ad9cb0456447
Source dataset
uspto-grants-1988_06
Patent number
US04752326

Reaction notes

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