Ammonium Chloride → HCID 178442047, compound

HRID 1359250Notes

Reaction equation

HRID 1359250 reaction equation
[CH2:1]([C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][C:7]=1[C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([O:25][CH2:26][C:27]#[N:28])[CH:19]=[CH:18]2)[CH2:2][CH2:3][CH2:4][CH3:5].[N-:29]=[N+:30]=[N-:31].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH2:1]([C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][C:7]=1[C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([O:25][CH2:26][C:27]1[NH:31][N:30]=[N:29][N:28]=1)[CH:19]=[CH:18]2)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18182803HCID 18182803, compound

Product 1

HCID 178442047HCID 178442047, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure described in Step 6, of Example 1, the title compound was prepared from [6-(3-pentyl-benzofuran-2-yl)-naphthalen-2-yloxy]-acetonitrile (0.2 g, 0.54 mmol), sodium azide (0.35 g, 5.4 mmol) and ammonium chloride (0.29 g, 5.4 mmol) in DMF (12 mL). The title compound was obtained as a white solid (0.085 g), mp 178-180° C. Mass spectrum (+APCl, [M+H]+) m/z 413. 1HNMR (400 MHz, DMSO-d6): δ8.27 (s, 1H), 8.03 (d, 1H, J=9.1 Hz), 7.97-7.87 (m, 2H), 7.68 (d, 1H, J=7.0 Hz), 7.61-7.56 (m, 2H), 7.36-7.25 (m, 3H), 5.63 (s, 2H), 2.96 (t, 2H, J=7.9 Hz), 1.72 (p, 2H, J=7.0 Hz), 1.41-1.29 (m, 4H), and 0.83 ppm (t, 3H, J=7.1 Hz). Elemental Analysis for C25H24N4O2.0.75H2O: Calculated: C, 70.49; H, 6.03; N, 13.15. Found: C, 70.18; H, 5.68; N, 13.3.

Sources & evidence

ORD record
ord-278125b7e2ad4191bbc534a8b0aaae03
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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