Benzyl Bromide → HCID 54316841, compound

HRID 1005447Notes

Reaction equation

HRID 1005447 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1.CN1CCCN(C)C1=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([O:16][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 7393741-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

Product 1

HCID 54316841HCID 54316841, compoundYield 7.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent2×

Procedure

670 mg (2.62 mmol) of 1-(2,4-dichlorophenyl)-2-[1,2,4]triazol-1-yl-ethanone in 12 ml of tetrahydrofuran and 4 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone were added to a suspension of 171 mg (3.92 mmol) of sodium hydride (55% in mineral oil) in 15 ml of tetrahydrofuran and 5 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) and stirred at room temperature for 3 hours. Thereafter, 396 mg (5.24 mmol) of benzyl bromide were added and the mixture was stirred at room temperature for a further 16 hours. The tetrahydrofuran was removed under a vacuum, the residue was added to 50 ml of water and extracted three times with 50 ml of diethyl ether each time. The combined organic phases were dried over magnesium sulphate and the diethyl ether was removed in a vacuum. The crude product was purified by column chromatography on silica gel (diethyl ether/pentane 1:4). In addition to mixed fractions with the C-alkylation product there were obtained 65 mg (7%) of pure 1-[2-(2,4-dichloro-phenyl)-2-benzyloxy-vinyl]-1H-[1,2,4]triazole as a colourless oil. [M+H]+ =345, 347.

Workup

  1. stirringthe mixture was stirred at room temperature for a further 16 hours
  2. customThe tetrahydrofuran was removed under a vacuum
  3. additionthe residue was added to 50 ml of water
  4. extractionextracted three times with 50 ml of diethyl ether each time
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. customthe diethyl ether was removed in a vacuum
  7. customThe crude product was purified by column chromatography on silica gel (diethyl ether/pentane 1:4)
  8. additionIn addition
  9. additionto mixed fractions with the C-alkylation product

Sources & evidence

ORD record
ord-d0024caca21c409d8cd37f4762568a23
Source dataset
uspto-grants-2000_04
Patent number
US06054588

Reaction notes

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