Ammonium Chloride → HCID 178442046, compound

HRID 392292Notes

Reaction equation

HRID 392292 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[C:9]1[C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[CH:28]=[C:27]([O:32][CH2:33][C:34]#[N:35])[CH:26]=[CH:25]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:36]=[N+:37]=[N-:38].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[C:9]1[C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([O:32][CH2:33][C:34]3[NH:38][N:37]=[N:36][N:35]=3)[CH:28]=2)[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 22327340{[6-(1-benzyl-3-pentyl-1H-indol-2-yl)-2-naphthyl]oxy}acetonitrile

Product 1

HCID 178442046HCID 178442046, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
97.5 °C

Procedure

To a stirred solution of the {[6-(1-benzyl-3-pentyl-1H-indol-2-yl)-2-naphthyl]oxy}acetonitrile (87.0 g, 189.71 mmol) in DMF (900 mL) under N2 was added NaN3 (61.665 g, 948.54 mmol) and NH4Cl (50.737 g, 948.54 mmol). The reaction was heated between 95-100° C. for 1.33 h then cooled. The reaction mixture was rotovap'd to a residue and the residue partitioned between EtOAc (2000 mL) and 1 N HCl (600 mL). The layers were shaken, separated, and the organic layer washed with 1 N HCl (2×300 mL), H2O (3×300 mL), and brine (2×300 mL), dried over Na2SO4, filtered, rotovap'd and triturated with hexane to give an off-white solid (97.5 g). The product was purified by refluxing the solid in diethyl ether (2000 mL), concentrating to about a liter and cooling. The solids were collected and dried in vacuo to give the product as a white solid (77.4 g, 154.3 mmol, 81%) with dec. 111-114° C.; 1H NMR (DMSO-d6) δ 0.72 (t, J=6.9 Hz, 3H) 1.10-1.20 (m, 4H), 1.50-1.60 (m, 2H), 2.67 (t, J=7.8 Hz, 2H), 5.30 (s, 2H), 5.62 (s, 2H), 6.81 (d, J=7.3 Hz, 2H), 7.02-7.20 (m, 5H), 7.30 (dd, J=2.4, 9.0 Hz, 1H), 7.35 (d, J=7.9 Hz, 1H), 7.44 (dd, J=1.5, 8.2 Hz, 1H), 7.55 (d, J=2.3 Hz, 1H), 7.60 (d, J=7.6 Hz, 1H), 7.84-7.90 m, 3H) 16.9 (s, 1H); IR (solid) 2920, 2850, 1610, 1390, 1200, 860, and 750, cm1; mass spectrum [ESI], m/z 502 (M+H)+;

Workup

  1. temperaturethen cooled
  2. customthe residue partitioned between EtOAc (2000 mL) and 1 N HCl (600 mL)
  3. customseparated
  4. washthe organic layer washed with 1 N HCl (2×300 mL), H2O (3×300 mL), and brine (2×300 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customtriturated with hexane

Sources & evidence

ORD record
ord-56b189c04adc45c78dce4e7968b4fbf8
Source dataset
uspto-grants-2004_10
Patent number
US06800654B2

Reaction notes

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