Ammonium Chloride → HCID 178506220, compound

HRID 269385Notes

Reaction equation

HRID 269385 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:14]=[C:13]2OCC#N.[N-:28]=[N+:29]=[N-:30].[Na+].[NH4+:32].[Cl-]>CN(C=O)C>[O:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:14]=[C:13]2[CH:2]([O:1][CH:5]([C:4]1[NH:32][N:30]=[N:29][N:28]=1)[C:13]1[C:12]2[C:17](=[CH:18][CH:19]=[C:10]([C:2]3[O:1][C:9]4[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=4[CH:3]=3)[CH:11]=2)[N:16]=[C:15]([C:20]([F:22])([F:21])[F:23])[CH:14]=1)[C:3]1[NH:32][N:30]=[N:29][N:28]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68961424HCID 68961424, compound

Product 1

HCID 178506220HCID 178506220, compoundYield 118.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of {[6-(1-benzofuran-2-yl)-2-(trifluoromethyl)quinolin-4-yl]oxy}acetonitrile (0.200 g, 0.543 mmol) in DMF (10 mL) at room temperature was added sodium azide (0.177 g, 2.72 mmol) followed by NH4Cl (0.145 g, 2.72 mmol). The reaction was heated to 100° C. for 2 hours. The mixture was concentrated and diluted with 2 N HCl (˜5 mL). This mixture was stirred at room temperature for 1 hour. The solid which formed was filtered and then washed with excess H2O and hexane and dried under high vacuum to afford the product (0.173 g, 78%) as a yellow solid, mp>225° C. (dec.), mp>225° C. (dec.). Mass spectrum (+APCI, [M+H]+) m/z 412. 1H NMR (500 MHz, DMSO-d6): δ 15.44-17.96 (br s, 1H), 8.72 (d, 1H, J=2.0 Hz), 8.46 (dd, 1H, J=2.0, 9.0 Hz), 8.21 (d, 1H, J=8.8 Hz), 7.70-7.75 (m, 3H), 7.76 (s, 1H), 7.38 (t, 1H, J=7.7 Hz), 7.30 (t, 1H, J=7.9 Hz,), and 6.04 ppm (s, 2H). Elemental analysis for C20H12F3N5O2.0.5H2O: Calculated: C, 57.15; H, 3.12; N, 16.66. Found: C, 57.43; H, 2.72; N, 16.53.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with 2 N HCl (˜5 mL)
  3. customThe solid which formed
  4. filtrationwas filtered
  5. washwashed with excess H2O and hexane
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-7c052aaecbf14f23a59e1be1e69b30c9
Source dataset
uspto-grants-2008_11
Patent number
US07446201B2

Reaction notes

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