Ammonium Chloride → HCID 178420507, compound

HRID 345930Notes

Reaction equation

HRID 345930 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:30]=[CH:29][C:16]([O:17][CH2:18][C:19]2[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=2)[O:22][CH2:23][C:24]#[N:25])=[CH:15][CH:14]=1.[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-].[NH4+]>CN(C)C=O.C(OCC)(=O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:30]=[CH:29][C:16]([O:17][CH2:18][C:19]2[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=2)[O:22][CH2:23][C:24]2[NH:33][N:32]=[N:31][N:25]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 14774149alpha-(3-(4-(2-Quinolinylmethyloxy)phenoxymethyl)phenoxy)acetonitrile

Product 1

HCID 178420507HCID 178420507, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

α-(3-(4-(2-quinolinylmethyloxy)phenoxymethyl)phenoxy)acetonitrile (8.12 mmol), sodium azide (24.4 mmol) and ammonium chloride (24.4 mmol) in dimethylformamide (10 ml) are heated at 115°-120° C. for 6 hrs. After cooling, the reaction mixture is diluted with ethyl acetate (150 ml), washed with water (6×100 ml) then dried and evaporated. The residue is chromatographed on a column of silica gel (360 g) and eluted with a gradient of isopropanol in methylene chloride to give 5-(3-(4-(2-quinolinylmethyloxy)phenoxymethyl)phenoxymethyl)tetrazole (M.P. 131°-132° C.)

Workup

  1. temperatureAfter cooling
  2. washwashed with water (6×100 ml)
  3. customthen dried
  4. customevaporated
  5. customThe residue is chromatographed on a column of silica gel (360 g)
  6. washeluted with a gradient of isopropanol in methylene chloride

Sources & evidence

ORD record
ord-7a8f1fb56c1d40a59d4dae84477bc2f1
Source dataset
uspto-grants-1991_10
Patent number
US05059610

Reaction notes

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