Azobisisobutyronitrile → Tebuconazole

HRID 1248860Notes

Reaction equation

HRID 1248860 reaction equation
[OH-].[Na+].N(C(C)(C)C#N)=NC(C)(C)C#N.[C:15]([C:19]1([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[CH2:21][O:20]1)([CH3:18])([CH3:17])[CH3:16].[NH:31]1[CH:35]=[N:34][CH:33]=[N:32]1>CN1CCCC1=O>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][CH2:22][C:19]([CH2:21][N:31]2[CH:35]=[N:34][CH:33]=[N:32]2)([OH:20])[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 92571H-1,2,4-TriazoleHCID 14798Sodium HydroxideHCID 946842-tert-Butyl-2-(2-(4-chlorophenyl)ethyl)oxirane

Product 1

HCID 86102TebuconazoleYield 85.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
120 °C

Procedure

4.15 g (0.103 mole) of sodium hydroxide and a spatula-tip of azo-bis-isobutyronitrile were added to a solution of 71.55 g (0.3 mole) of 2-tert.-butyl-2-(4-chloro-phenyl-ethyl)-oxirane in 10 ml of N-methylpyrrolidone. The mixture was heated to 120° C. and a solution of 20.7 g (0.3 mole) of 1,2,4-triazole was added dropwise in the course of 3 hours, with stirring. The mixture was then stirred at 120° C. for a further hour and then allowed to cool. Thereafter, it was worked up by a procedure in which the N-methyl-pyrrolidone was distilled off at a bath temperature of 100° C. under a pressure of 0.2 mbar 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. 78.9 g (85.8% 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. stirringThe mixture was then stirred at 120° C. for a further hour
  2. temperatureto cool
  3. distillationwas distilled off at a bath temperature of 100° C. under a pressure of 0.2 mbar
  4. washthe residue which remained was washed with water
  5. customdried
  6. stirringstirred with 150 ml of benzine
  7. filtrationThe solid product which deposited was filtered off
  8. customdried again

Sources & evidence

ORD record
ord-eede497dc5964b2db073400ffddca3de
Source dataset
uspto-grants-1986_12
Patent number
US04626594

Reaction notes

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