Acetic Anhydride → N-{2-phenyl-2-[(1,2,4-triazol-1-yl)methyl]hexyl}acetamide

HRID 54909Notes

Reaction equation

HRID 54909 reaction equation
[C:1]1([C:7]([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>N1C=CC=CC=1>[C:1]1([C:7]([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:8][NH:9][C:20](=[O:22])[CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 199569622-Phenyl-2-[(1,2,4-triazol-1-yl)methyl]-1-hexylamine

Product 1

HCID 15790295N-{2-phenyl-2-[(1,2,4-triazol-1-yl)methyl]hexyl}acetamideYield 89.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a 100 mL flask stirring under nitrogen was charged 2.58 g (0.010 mole) of 2-phenyl-2-[(1,2,4-triazol-1-yl)methyl]-1-hexylamine and 15 mL of acetic anhydride. To the mixture was added 1.5 mL of pyridine and the reaction was stirred at room temperature for 3 hours. After GLC indicated the reaction was complete, it was quenched with 20 mL of water and 100 mL of ether after the acetic anhydride and pyridine were removed under vacuum. The residue was dissolved in ether and washed with 2×50 mL water and 2×50 mL of saturated sodium bicarbonate. The organic phase was dried, concentrated and gave 2.68 g (89.3% yield) of a solid, melting point 112°-115° C.

Workup

  1. stirringthe reaction was stirred at room temperature for 3 hours
  2. customit was quenched with 20 mL of water and 100 mL of ether after the acetic anhydride and pyridine
  3. customwere removed under vacuum
  4. dissolutionThe residue was dissolved in ether
  5. washwashed with 2×50 mL water and 2×50 mL of saturated sodium bicarbonate
  6. customThe organic phase was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fc16da06b4e44ace8da0106784417fd8
Source dataset
uspto-grants-1997_04
Patent number
US05624916

Reaction notes

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