Sodium Azide → 4-(Azidomethyl)benzaldehyde

HRID 1509359Notizen

Reaktionsgleichung

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]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-57c9054ecca34e719e4decb6b9b6c5b5
Quelldatensatz: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09222941B2

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