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Hexane → 5-Carbomethoxy-2-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]propyl]-1,2,4-triazole

HRID 741655
Notes
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Reaction equation

HRID 741655 reaction equation
CCCCCC.[H-].[Na+].[C:9]([C:13]1[NH:17][N:16]=[CH:15][N:14]=1)([O:11][CH3:12])=[O:10].[CH3:18][N:19]1[N:23]=[N:22][C:21]([C:24]2[CH:34]=[C:33]([CH3:35])[C:27]([O:28][CH2:29][CH2:30][CH2:31]Br)=[C:26]([CH3:36])[CH:25]=2)=[N:20]1>CN(C=O)C>[C:9]([C:13]1[N:14]=[CH:15][N:16]([CH2:31][CH2:30][CH2:29][O:28][C:27]2[C:26]([CH3:36])=[CH:25][C:24]([C:21]3[N:22]=[N:23][N:19]([CH3:18])[N:20]=3)=[CH:34][C:33]=2[CH3:35])[N:17]=1)([O:11][CH3:12])=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 2735089methyl 1H-1,2,4-triazole-3-carboxylateHCID 153915233-[4-(2-Methyltetrazol-5-yl)-2,6-dimethylphenoxy]-propylbromide

Product 1

HCID 221033915-Carbomethoxy-2-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]propyl]-1,2,4-triazoleYield 40%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent3×

Procedure

Hexane washed 60% NaH (22 mg, 0.55 mmol) in 0.5 ml of DMF was added at 20° C. to a solution of 5-carbomethoxy-1,2,4-triazole (63.5 mg, 0.5 mmol) in 0.5 ml of DMF and the mixture was stirred for 1 h. To the above mixture was added at 20° C. 3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propylbromide (163 mg, 0.5 mmol) in 0.5 ml of DMF and the mixture was stirred at 20° C. for 18 h. The mixture was partitioned between ice/water and ethyl acetate. The aqueous layer was extracted with ethyl acetate (3×), and the organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica column chromatography (20 cm column, ethyl acetate/hexane, 1/5-1/0; methylene chloride/acetone) to afford 74 mg (40%) of 5-carbomethoxy-2-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]propyl]-1,2,4-triazole.

Workup

  1. additionTo the above mixture was added at 20° C
  2. customThe mixture was partitioned between ice/water and ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica column chromatography (20 cm column, ethyl acetate/hexane, 1/5-1/0; methylene chloride/acetone)

Sources & evidence

ORD record
ord-f4b2938f564e475fa3806dd33a1d0671
Source dataset
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05552420

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes