Ammonium Chloride → HCID 178442047, compound

HRID 1359256Notes

Reaction equation

HRID 1359256 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:25]=[CH:24][CH:23]=[CH:22][C:15]=4[C:16]=3[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:26][CH2:27][C:28]#[N:29].[N-:30]=[N+:31]=[N-:32].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH2:17]([C:16]1[C:15]2[CH:22]=[CH:23][CH:24]=[CH:25][C:14]=2[O:13][C:12]=1[C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[CH:2]=[C:3]([O:26][CH2:27][C:28]1[NH:29][N:32]=[N:31][N:30]=1)[CH:4]=[CH:5]2)[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18182777HCID 18182777, compound

Product 1

HCID 178442047HCID 178442047, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure described in Step 6, of Example 1, the title compound was prepared from [1-bromo-6-(3-pentyl-benzofuran-2-yl)-naphthalen-2-yloxy]-acetonitrile (1.23 g, 2.75 mmol), sodium azide (1.8 g, 27.5 mmol) and ammonium chloride (1.45 g, 27.5 mmol) in DMF (30 mL). Crystallization from methanol afforded the title compound as an off-white solid (0.75 g), mp 192-194° C. Mass spectrum (+APCl, [M+H]+) m/z 491. 1HNMR (400 MHz, DMSO-d6): δ8.36 (d, 1H, J=1.5 Hz), 8.23-8.17 (m, 2H), 8.05 (dd, 1H, J=9.0, 1.7 Hz), 7.72-7.68 (m, 2H), 7.61 (m, 1H, J=8.1 Hz), 7.37-7.27 (m, 2H), 5.75 (s, 2H), 3.00 (t, 2H, J=7.8 Hz), 1.74-1.767 (m, 2H), 1.42-1.26 (m, 4H), and 0.84-0.80 ppm (m, 3H). Elemental Analysis for C25H24N4O2.0.75H2O: Calculated: C, 59.47; H, 4.89; N, 11.09. Found: C, 59.51; H, 4.6; N, 11.09.

Workup

  1. customCrystallization from methanol

Sources & evidence

ORD record
ord-a9e1f54f462c418c813cc5e4984389e0
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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