1H-1,2,4-Triazole → 3,4-Dihydro-2-(1H-1,2,4-triazole-1-yl)1(2H)-Naphthalenone

HRID 248767

Reaction equation

HRID 248767 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH:11]=[N:10][CH:9]=[N:8]1.Br[CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23]>C(#N)C.ClCCl>[N:7]1([CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])[CH:11]=[N:10][CH:9]=[N:8]1

Participants

6

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 1011201(2H)-Naphthalenone, 2-bromo-3,4-dihydro-

Product 1

HCID 146988003,4-Dihydro-2-(1H-1,2,4-triazole-1-yl)1(2H)-Naphthalenone

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 30 g. potassium carbonate, 15 g. 1,2,4-triazole and 250 ml acetonitrile at 40° C. was added a solution of 45 g. 3,4-dihydro-2-bromo-1(2H)-naphthalenone in 150 ml acetonitrile. The mixture was allowed to react for 5 hours at 40° C. and than at reflux temperature for 2 hours. The solid was removed by filtration and the filtrate concentrated to dryness leaving a solid residue. This was dissolved in dichloromethane and washed twice with water. The organic extract was dried over sodium sulfate and evaporated to give 42 grams of product having a melting point of 96°-98° C.

Workup

  1. additionTo a mixture of 30 g
  2. customto react for 5 hours at 40° C.
  3. temperaturethan at reflux temperature for 2 hours
  4. customThe solid was removed by filtration
  5. concentrationthe filtrate concentrated to dryness
  6. customleaving a solid residue
  7. washwashed twice with water
  8. extractionThe organic extract
  9. dry with materialwas dried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-03d5c0cd105e4024bc952133e486760d
Source dataset
uspto-grants-1993_05
Patent number
US05211736

Linked notes

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