Ammonium Chloride → HCID 178446891, compound

HRID 1359200Notes

Reaction equation

HRID 1359200 reaction equation
[C:1]([C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][C:8]=1[C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([O:26][CH2:27][C:28]#[N:29])[CH:20]=[CH:19]2)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[N-:30]=[N+:31]=[N-:32].[Na+].[Cl-].[NH4+]>CN(C=O)C>[NH:30]1[C:28]([CH2:27][O:26][C:21]2[CH:22]=[C:23]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[C:16]([C:8]2[O:9][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[C:7]=2[C:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5])[CH:25]=[CH:24]3)=[N:29][N:32]=[N:31]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 120828322-{[6-(3-Pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile

Product 1

HCID 178446891HCID 178446891, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure described in Step 6 of Example 1, the title compound was prepared from 2-{[6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile (0.350 g, 0.913 mmol), sodium azide (0.297 g, 4.56 mmol), and ammonium chloride (0.246 g, 4.60) mmol) in DMF (6 mL). Crystallization from acetonitrile (also using charcoal), and drying of the product for 16 hours at 84° C. yielded a light yellow solid (0.0978 g), mp 150-151° C. Mass spectrum (+APCl, [M+H]+) m/z427; 1HNMR (400 MHz, DMSO-d6): δ16.8-17.1 (br, 1H), 8.4 (d, 1H, J=1.2 Hz), 8.0-8.05 (m, 3H), 7.85 (dd, 1H, J=8.5 Hz and 1.7 Hz), 7.7 (d, 1H, J=7.5 Hz), 7.65 (d, 1H, J=2.4 Hz) 7.45 (m, 3H), 5.65 (s, 2H), 2.75 (t, 2H, J=7.3 Hz), 1.5-1.6 (m, 2H), 1.1-1.2(m, 2H), and 0.7 ppm (t, 3H, J=7.4 Hz). Elemental Analysis for C25H22N4O3: Calculated: C, 70.41;H, 5.20; N, 13.14. Found: C, 70.21;H, 5.14; N, 13.23.

Workup

  1. customCrystallization from acetonitrile (also using charcoal), and
  2. customdrying of the product for 16 hours at 84° C.

Sources & evidence

ORD record
ord-3a5a861bc6554c3fa78348b1e09be689
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

Loading…