Sodium Azide → HCID 91277700, compound

HRID 1890165Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:5][CH:4]=1.[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C=O)C>[N:24]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:5][CH:4]=1)=[N+:25]=[N-:26]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 1-(4-(chloromethyl)phenyl)-2,5,8,11,14-pentaoxapentadecane (1.50 g, 4.33 mmol) in DMF (10 mL) was added NaN3 (337.9 mg, 5.20 mmol). The reaction mixture was stirred overnight at 110° C. The solvent was subsequently evaporated. The residue was then suspended in ethyl acetate and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography to give the desired azide (1.53 g, 4.33 mmol, 90%) as a colorless liquid. 1H NMR (300 MHz, CDCl3) δ 7.37 (d, 2H, J=8.0 Hz), 7.30 (d, 2H, J=8.2 Hz), 4.58 (s, 2H), 4.33 (s, 2H), 3.69−3.58 (m, 14H), 3.56−3.52 (m, 2H), 3.37 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 138.6, 134.7, 128.3, 128.2, 72.9, 72.0, 70.7, 70.6, 70.5, 69.7, 68.0, 59.1, 54.6; MS (ESI) m/z calcd for C17H27N3O5 [M+H]+ 353.2 found [M+H2O]+ 371.2.

Workup

customThe solvent was subsequently evaporated
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-fbc649d850ae4736a5b4caf7c1f80631
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08506993B2

Reaction notes

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