Carbon Dioxide → Tebuconazole

HRID 1248861Notes

Reaction equation

HRID 1248861 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[OH-].[Na+].[C:8]([C:12]1([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:14][O:13]1)([CH3:11])([CH3:10])[CH3:9].C(=O)=O>CN1CCCC1=O.O>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][CH2:15][C:12]([CH2:14][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)([OH:13])[C:8]([CH3:10])([CH3:9])[CH3:11])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 92571H-1,2,4-TriazoleHCID 14798Sodium HydroxideHCID 946842-tert-Butyl-2-(2-(4-chlorophenyl)ethyl)oxirane

Product 1

HCID 86102TebuconazoleYield 88.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

20.7 g (0.3 mole) of 1,2,4-triazole, 4.15 g (0.103 mole) of sodium hydroxide and 1 ml of water were added to a solution of 71.55 g (0.3 mole) of 2-tert.-butyl-2-(4-chloro-phenyl-ethyl)-oxirane in 125 ml of N-methyl-pyrrolidone at room temperature, with stirring. The reaction mixture was heated at 120° C. for 4 hours, with stirring, during which a dry stream of CO2 -free air was slowly passed through. Thereafter, the mixture was worked up by a procedure in which the solvent was distilled off under reduced pressure and the residue which remained was washed with water and then dried and stirred with 150 ml of benzine. The solid product which deposited was filtered off and dried again. 81.9 g (88.8% of theory) of 1-(4-chloro-phenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-yl-methyl)-pentan-3-ol were obtained in this manner.

Workup

  1. distillationwas distilled off under reduced pressure
  2. washthe residue which remained was washed with water
  3. customdried
  4. stirringstirred with 150 ml of benzine
  5. filtrationThe solid product which deposited was filtered off
  6. customdried again

Sources & evidence

ORD record
ord-688502b4ee3241429fbecc18dea6894a
Source dataset
uspto-grants-1986_12
Patent number
US04626594

Reaction notes

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