Dimethylformamide → HCID 178502648, compound

HRID 1387341Notes

Reaction equation

HRID 1387341 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].CN(C)C=O.[CH3:12][C:13]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[N:26][O:27][CH3:28])[C:24]#[N:25]>C(OCC)(=O)C>[CH3:28][O:27][N:26]=[C:23]([C:24]1[NH:25][N:3]=[N:2][N:1]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][O:15][C:14]1[CH:29]=[C:30]([CH3:33])[CH:31]=[CH:32][C:13]=1[CH3:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 54390956HCID 54390956, compound

Product 1

HCID 178502648HCID 178502648, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

Sodium azide (1.30 g, 20 mmol), ammonium chloride (1.07 g, 20 mmol) and N,N-dimethylformamide (10 ml) were added to 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetonitrile (0.59 g, 2 mmol), and the mixture was stirred at 115° C. for 9 hours. After completion of the reaction, ethyl acetate (150 ml) was added, and the mixture was washed with saturated brine (100 ml) twice. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give 2-(2,5-dimethylphenoxymethyl)phenyl 1H-tetrazol-5-yl ketone O-methyloxime (0.59 g, 87.4%) as colorless crystals.

Workup

  1. additionwas added
  2. washthe mixture was washed with saturated brine (100 ml) twice
  3. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-435a36cb8c9f448fa64a5a612f463087
Source dataset
uspto-grants-2001_07
Patent number
US06268312B1

Reaction notes

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