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

HRID 54902Notes

Reaction equation

HRID 54902 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-propanenitrile followed by 100 mL (0.63 moles) 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 diluted with 200 mL of ethyl acetate. The organic phase (3×200 mL ethyl acetate) was washed with 100 mL of water (3×). 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, melting point 170°-172° C.

Workup

  1. temperatureat reflux for 48 hours after which GLC
  2. customA gummy oil formed which
  3. washThe organic phase (3×200 mL ethyl acetate) was washed with 100 mL of water (3×)
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customto give a tan solid which
  7. customwas recrystallized from ethyl ether
  8. filtrationThe product was filtered

Sources & evidence

ORD record
ord-3977f756182c49d8a16e2388e21d7ccf
Source dataset
uspto-grants-1997_04
Patent number
US05624916

Reaction notes

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