Water → HCID 178428967, compound

HRID 1514885Notes

Reaction equation

HRID 1514885 reaction equation
[CH:1]([C:3]1[C:12]([CH3:13])=[CH:11][C:6]([O:7][CH2:8][C:9]#[N:10])=[CH:5][C:4]=1[CH3:14])=[O:2].[N-:15]=[N+:16]=[N-:17].[Na+].[Cl-].[NH4+].O>CN(C=O)C>[CH3:14][C:4]1[CH:5]=[C:6]([O:7][CH2:8][C:9]2[NH:17][N:16]=[N:15][N:10]=2)[CH:11]=[C:12]([CH3:13])[C:3]=1[CH:1]=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86651260(4-Formyl-3,5-dimethyl-phenoxy)-acetonitrile

Product 1

HCID 178428967HCID 178428967, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (4-formyl-3,5-dimethyl-phenoxy)-acetonitrile (120 mg) in DMF (3 mL) were added sodium azide (62 mg) and ammonium chloride (51 mg). The reaction mixture was heated at 100° C. for 1 h. The mixture was then diluted by water and the whole was loaded onto a cartridge that contained C18 silica gel (reverse phase). Wash-to-waste (10 mL water) was followed by elute-to-collect (10 mL, acetonitrile) and, after evaporation of volatiles, 2,6-dimethyl-4-(1H-tetrazol-5-yl-methoxy)-benzaldehyde was obtained.

Workup

  1. washWash-to-waste (10 mL water)
  2. customby elute-to-collect (10 mL, acetonitrile)
  3. customafter evaporation of volatiles

Sources & evidence

ORD record
ord-7a575fa8479b46d6b2c8fe0df30a9c43
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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