Sulfuric Acid → 2-(4-Chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexanamide

HRID 2211086Notes

Reaction equation

HRID 2211086 reaction equation
[CH2:1]([C:5]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)([CH2:8][N:9]1[CH:13]=[N:12][CH:11]=[N:10]1)[C:6]#[N:7])[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)[OH:22]>[OH-].[NH4+]>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:5]([CH2:8][N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([NH2:7])=[O:22])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 6336Myclobutanil

Product 1

HCID 199569562-(4-Chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexanamideYield 56.5%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

To a 500 mL flask was charged 75.0 g (0.24 mole) of alpha-n-butyl-alpha-(4-chlorophenyl)-1H-1,2,4-triazole-1-propanenitrile followed by 300 mL of 95% sulfuric acid. The mixture was stirred at 90° C. for 7 days after which the mixture was cooled to room temperature, diluted with ice and neutralized with ammonium hydroxide until basic (pH 8). The product was extracted with ethylene dichloride then washed with water and dried over magnesium sulfate. The solvent was concentrated and gave 45 g (56.5% yield) of a solid melting point 197°-199° C.

Workup

  1. temperaturewas cooled to room temperature
  2. extractionThe product was extracted with ethylene dichloride
  3. washthen washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-f650dc212762457fa3f6cda6e0c69aa4
Source dataset
uspto-grants-1995_10
Patent number
US05462931

Reaction notes

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