Ammonium Chloride → HCID 178510078, compound

HRID 1357374Notes

Reaction equation

HRID 1357374 reaction equation
[Cl-].[NH4+].[N-:3]=[N+:4]=[N-:5].[Na+].[NH2:7][C:8]1[CH:24]=[CH:23][CH:22]=[CH:21][C:9]=1[O:10][C:11]1[CH:12]=[C:13]([C:19]#[N:20])[C:14](=[CH:17][CH:18]=1)[C:15]#[N:16]>CN(C=O)C>[C:19]([C:13]1[CH:12]=[C:11]([CH:18]=[CH:17][C:14]=1[C:15]1[NH:16][N:5]=[N:4][N:3]=1)[O:10][C:9]1[CH:21]=[CH:22][CH:23]=[CH:24][C:8]=1[NH2:7])#[N:20].[C:15]([C:14]1[CH:17]=[CH:18][C:11]([O:10][C:9]2[CH:21]=[CH:22][CH:23]=[CH:24][C:8]=2[NH2:7])=[CH:12][C:13]=1[C:19]1[NH:20][N:5]=[N:4][N:3]=1)#[N:16]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18506202HCID 18506202, compound

Product 2

HCID 178510078HCID 178510078, compoundHCID 178510234HCID 178510234, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Ammonium chloride (0.46 g, 8.5 mmol) and sodium azide (0.55 g, 8.5 mmol) were added to a solution of 4-(2-aminophenoxy)phthalonitrile (0.5 g, 2.1 mmol) in DMF (20 ml). The reaction mixture was heated at 80° C. for 48 hours, cooled to room temperature and evaporated to dryness in vacuo. The crude compound was purified on silica gel (eluent: methylene chloride:methanol (4:1)) to give 2-[3-cyano-4-(1H-tetrazol-5yl)phenoxy]aniline or 2-[4-cyano-3-(1H-tetrazol-5-yl)phenoxy]aniline as yellow crystals (yield: 0.64 g (95%)). 1H—NMR (CD3OD) in ppm: δ 5.2 (2H,s), 6.6 (1H, d,d), 6.85 (1H,d,d), 6.95 (1H,d,d.), 7.0 (1H,d,d.), 7.45 (1H,d), 7.65 (1H,d). 13C—NMR (CD3OD) in ppm: δ 105.3; 118.7; 119.4; 119.7; 120.7; 123.0; 128.3; 133.3; 138.3; 138.3; 140.7; 142.8; 158.9; 163.4.

Workup

  1. temperaturecooled to room temperature
  2. customevaporated to dryness in vacuo
  3. customThe crude compound was purified on silica gel (eluent: methylene chloride:methanol (4:1))

Sources & evidence

ORD record
ord-1ce03440dabe4ab0a7f5cd040b7e74b0
Source dataset
uspto-grants-2003_07
Patent number
US06590118B1

Reaction notes

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