Sodium Azide → 4-(Azidomethyl)benzaldehyde

HRID 1509359Notes

Reaction equation

HRID 1509359 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C.C(OCC)(=O)C.O>[N:11]([CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1)=[N+:12]=[N-:13]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 112064214-(Bromomethyl)benzaldehyde

Product 1

HCID 574448534-(Azidomethyl)benzaldehydeYield 92.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Bromide 3 (180 mg, 0.90 mmol) was dissolved in DMF (10 ml). Sodium azide (88 mg, 1.35 mmol) was added. The reaction mixture was then heated at 60° C. for an hour. The reaction mixture was allowed to cool and was dissolve in ethyl acetate (150 ml) and H2O (150 ml). The phases were separated and the organic phase was washed again with water (2×150 ml). The organic phase was dried over sodium sulphate, and evaporated under reduced pressure to yield 4 as an oil (134 mg, 0.83 mmol, 92%). Rf=0.70 (DCM); νmax=2094, 1694, 1607, 1207, 1167, 812, 773 cm−1; 1H NMR (300 MHz, CDCl3) δ=10.02 (s, 1H, CHO), 7.90 (d, 3J(H,H)=7.9 Hz, 2H, ArCH α to CHO), 7.48 (d, 3J(H,H)=7.9 Hz, 2H, ArCH α to CH2N3), 4.45 (s, 2H, CH2N3); 13C NMR (75 MHz, CDCl3) δ=191.6 (CHO), 142.1 (ArCCH2N3), 136.2 (ArCCHO), 130.2 (ArCH α to ArCCHO), 128.4 (ArCH α to ArCCH2N3), 54.2 (CH2N3); HRMS (ESI+): m/z calculated for C8H7N3ONa [M+Na]+: 184.0481, found 184.0497.

Workup

  1. temperatureto cool
  2. customThe phases were separated
  3. washthe organic phase was washed again with water (2×150 ml)
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-57c9054ecca34e719e4decb6b9b6c5b5
Source dataset
uspto-grants-2015_12
Patent number
US09222941B2

Reaction notes

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