Triethylamine → HCID 12899889, compound

HRID 2198774Notes

Reaction equation

HRID 2198774 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][CH:5]([N:13]1[CH:17]=[N:16][CH:15]=[N:14]1)[CH:6]([OH:12])[C:7]([CH3:11])([CH3:10])[CH2:8][F:9].[CH3:23][N:24]=[C:25]=[O:26].C(N(CC)CC)C>O1CCOCC1>[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][CH:5]([N:13]1[CH:17]=[N:16][CH:15]=[N:14]1)[CH:6]([O:12][C:25](=[O:26])[NH:24][CH3:23])[C:7]([CH3:11])([CH3:10])[CH2:8][F:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 12899885HCID 12899885, compound

Product 1

HCID 12899889HCID 12899889, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

8.4 g (0.024 mol) of 1-(2,4-dichlorophenoxy)-3,3-dimethyl-4-fluoro-1-(1,2,4-triazol-1-yl)-butan-2-ol were dissolved in 100 ml of dioxane, and 2 ml of methyl isocyanate and 3.5 ml of triethylamine were added. The mixture was heated under reflux for 10 hours and concentrated by distilling off the solvent in vacuo. The residue was heated in 50 ml of ethyl acetate and the mixture was filtered. 8 g (86% of theory) of 1-(2,4-dichlorophenoxy)-3,3-dimethyl-4-fluoro-2-methylcarbamoyloxy-1-(1,2,4-triazol-1-yl)-butane were obtained in the form of colorless crystals of melting point 124°-27° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 10 hours
  3. concentrationconcentrated
  4. distillationby distilling off the solvent in vacuo
  5. temperatureThe residue was heated in 50 ml of ethyl acetate
  6. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-21e22aa5c6d3495e9620a0be8d6413ff
Source dataset
uspto-grants-1982_11
Patent number
US04359470

Reaction notes

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