Ammonium Hydroxide → (+/-)-4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]-benzenamine

HRID 586432Notes

Reaction equation

HRID 586432 reaction equation
[CH3:1][CH:2]([CH3:19])[CH:3]([C:9]1[CH:14]=[CH:13][C:12]([NH:15]C(=O)C)=[CH:11][CH:10]=1)[N:4]1[CH:8]=[N:7][CH:6]=[N:5]1.[NH4+].[OH-]>Cl>[CH3:1][CH:2]([CH3:19])[CH:3]([C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)[N:4]1[CH:8]=[N:7][CH:6]=[N:5]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 9903273(+/-)-N-[4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]phenyl]acetamide

Product 1

HCID 10900053(+/-)-4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]-benzenamineYield 75.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (±)-N-[4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]phenyl]acetamide (0.095 mol) in HCl (3N) (250 ml) was stirred and heated at 60° C. for 5 hours. The mixture was cooled, poured into ice, basified with concentrated NH4OH and extracted with CH2Cl2. The organic layer was dried, filtered off and evaporated. The residue was crystallized from 2-propanone/(C2H5)2O and filtered off, yielding 15.5g (75%) of (±)-4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]-benzenamine (interm. 2; mp. 117.8° C.).

Workup

  1. temperatureThe mixture was cooled
  2. additionpoured into ice
  3. extractionextracted with CH2Cl2
  4. customThe organic layer was dried
  5. filtrationfiltered off
  6. customevaporated
  7. customThe residue was crystallized from 2-propanone/(C2H5)2O
  8. filtrationfiltered off

Sources & evidence

ORD record
ord-8e8f1f7ea0aa4b939e21c2bc0b2e8200
Source dataset
uspto-grants-2005_08
Patent number
US06936626B2

Reaction notes

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