Diethyl Ether → N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

HRID 1503163Notes

Reaction equation

HRID 1503163 reaction equation
[Na].[CH2:2]([C:9]1[N:13]([CH3:14])[N:12]=[N:11][N:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O:20][N:21]=O)CC(C)C.CCOCC>C(O)C.O>[OH:20][N:21]=[C:2]([C:9]1[N:13]([CH3:14])[N:12]=[N:11][N:10]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8053Isoamyl NitriteHCID 5360545SodiumHCID 10012507HCID 10012507, compound

Product 1

HCID 135990939N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimineYield 46.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of sodium hydroxyde (115 mg, 2.9 mmol) in 1.5 mL ethanol was added 500 mg of 5-benzyl-1-methyl-1H-tetrazole (2.9 mmol). The mixture was stirred 15 min at room temperature. A solution of isoamylnitrite (353 mg, 3 mmol) in 1 mL ethanol was then added dropwise and the mixture was stirred at room temperature for 16 h. Ether and water were then added and the layers were separated. The aqueous phase was washed with ether and then acidified with HCl 0.1M. The resulting neutral solution was extracted 3 times with ethyl acetate. The organic layers were combined, dried over magnesium sulfate and concentrated to afford 272 mg of the title compound (Z:E mixture) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. customthe layers were separated
  3. washThe aqueous phase was washed with ether
  4. extractionThe resulting neutral solution was extracted 3 times with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7366923d4cc341b59e1ab438cc7b395a
Source dataset
uspto-grants-2015_12
Patent number
US09212152B2

Reaction notes

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