Water → N-[Phenyl-(phenylmethyl)methylene]-1H-1,2,4-triazol-1-amine

HRID 2248606Notes

Reaction equation

HRID 2248606 reaction equation
[NH2:1][N:2]1[CH:6]=[N:5][CH:4]=[N:3]1.[C:7]1([C:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1.CCOCC>[C:7]1([C:13]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:1][N:2]2[CH:6]=[N:5][CH:4]=[N:3]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 99482-PhenylacetophenoneHCID 117080471H-1,2,4-triazol-1-amine

Product 1

HCID 54338153N-[Phenyl-(phenylmethyl)methylene]-1H-1,2,4-triazol-1-amine

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 5.7 g (50.8 mmol) of 75% pure 1-amino-1H-1,2,4-triazole, 5.0 g (25.5 mmol) of deoxybenzoin and 0.6 g p-toluenesulfonic acid in 150 mL of benzene was heated at reflux with azeotropic removal of water for 7 days. Solvent was stripped and the residue was diluted with ether, which was washed with saturated aqueous Na2CO3, water and brine. Drying (MgSO4) and removal of solvent gave an off-white solid which was recrystallized from hexane affording 3.23 g of the desired product, m.p. 78°-80° C.

Workup

  1. washwas washed with saturated aqueous Na2CO3, water and brine
  2. customDrying
  3. custom(MgSO4) and removal of solvent
  4. customgave an off-white solid which
  5. customwas recrystallized from hexane affording 3.23 g of the desired product, m.p. 78°-80° C.

Sources & evidence

ORD record
ord-8052aa41a1004f5fa9ca92d7fcdd1129
Source dataset
uspto-grants-1991_08
Patent number
US05041458

Reaction notes

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