Hydrogen Bromide → 2-(2,4-Dichlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexanoamide

HRID 257724Notes

Reaction equation

HRID 257724 reaction equation
[CH2:1]([C:5]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])([CH2:8][N:9]1[CH:13]=[N:12][CH:11]=[N:10]1)[C:6]#[N:7])[CH2:2][CH2:3][CH3:4].Br.[OH-:23].[NH4+].Cl>C(OCC)(=O)C>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[C:5]([CH2:8][N:9]1[CH:13]=[N:12][CH:11]=[N:10]1)([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([NH2:7])=[O:23]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 13069855alpha-n-butyl-alpha-(2,4-dichlorophenyl)-1H-1,2,4-triazole-1-propanenitrile

Product 1

HCID 199569472-(2,4-Dichlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexanoamideYield 56.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 250 mL flask was charged 38.16 g (0.119 mole) of alpha-n-butyl-alpha-(2,4-dichlorophenyl)-1H-1,2,4-triazole-1-propane-nitrile followed by 100 mL (0.63 mole) of 48% hydrobromic acid. The mixture was stirred at reflux for 48 hours after which GLC indicated disappearance of the starting material. The reaction was cooled to room temperature and neutralized with concentrated ammonium hydroxide (100 mL) to pH 8 and then to neutral pH with concentrated hydrochloric acid. A gummy oil formed which was taken up with 200 mL of ethyl acetate. The aqueous was extracted twice more with 200 ml portions of ethyl acetate and the combined ethyl acetate portions were then washed three times with 100 mL portions of water. The organic phase was dried and concentrated to give a tan solid which was recrystallized from ethyl ether. The product was filtered and gave 22.78 g (56.3% yield) of a solid, Example 162 of Table 1.

Workup

  1. temperatureat reflux for 48 hours after which GLC
  2. customA gummy oil formed which
  3. extractionThe aqueous was extracted twice more with 200 ml portions of ethyl acetate
  4. washthe combined ethyl acetate portions were then washed three times with 100 mL portions of water
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. customto give a tan solid which
  8. customwas recrystallized from ethyl ether
  9. filtrationThe product was filtered

Sources & evidence

ORD record
ord-6d73a4b7c7854ff09052ecde90ebf5de
Source dataset
uspto-grants-1993_11
Patent number
US05264415

Reaction notes

Loading…