Ammonium Chloride → HCID 178519458, compound

HRID 1359237Notes

Reaction equation

HRID 1359237 reaction equation
[C:1]([C:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][C:10]=1[C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[C:24]([Br:28])=[C:23]([O:29][CH2:30][C:31]#[N:32])[CH:22]=[CH:21]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:33]=[N+:34]=[N-:35].[Na+].[NH4+].[Cl-]>CN(C=O)C>[Br:28][C:24]1[C:23]([O:29][CH2:30][C:31]2[NH:35][N:34]=[N:33][N:32]=2)=[CH:22][CH:21]=[C:20]2[C:25]=1[CH:26]=[CH:27][C:18]([C:10]1[O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:9]=1[C:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:8])=[CH:19]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18182805HCID 18182805, compound

Product 1

HCID 178519458HCID 178519458, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of {[6-(3-benzoyl-1-benzofuran-2-yl)-1-bromo-2-naphthyl]oxy} acetonitrile (0.174 g, 0.361 mmol) in DMF (10 mL) at room temperature was added NaN3 (0.117 g, 1.81 mmol) followed by NH4Cl (0.097 g, 1.81 mmol). The reaction was heated to 100° C. for 2 h. After this time, it was concentrated and diluted with 2 N HCl (˜5 mL). This mixture was stirred at room temperature for 1 h. The solid was filtered and washed with excess water and hexane then dried under high vacuum to afford the product (0.190 g, 99%) as a light. brown solid, mp>183° C. (dec.). Mass spectrum (+APCl, [M+NH4]+) m/z 542. 1HNMR (500 MHz, DMSO-d6): δ14.75-17.75 (br s, 1H), 8.28 (d, 1H, J=2.0 Hz), 8.03 (d, 1H, J=9.0 Hz), 8.00 (d, 1H, J=8.8 Hz), 7.78-7.83 (m, 3H), 7.76 (dd, 1H, J=1.7, 8.8 Hz), 7.67 (d, 1H, J=9.0 Hz), 755 (d, J=7.6 Hz, 1H), 7.32-7.38 (m, 3H), 7.45-7.52 (m, 2H), and 5.71 ppm (s, 2H). Elemental analysis for C27H17BrN4O3.1.0H2O: Calculated: C, 59.68; H, 3.52; N, 10.31. Found: C, 59.72; H, 3.23; N, 10.51.

Workup

  1. concentrationAfter this time, it was concentrated
  2. additiondiluted with 2 N HCl (˜5 mL)
  3. filtrationThe solid was filtered
  4. washwashed with excess water and hexane
  5. customthen dried under high vacuum

Sources & evidence

ORD record
ord-b3ab4722269f4a03b69eabc29ccfbf39
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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