Ammonium Chloride → HCID 178489193, compound

HRID 1653816Notes

Reaction equation

HRID 1653816 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[N-:28]=[N+:29]=[N-:30].[Na+].[Cl-].[NH4+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]3[NH:30][N:29]=[N:28][N:27]=3)[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 20080536HCID 20080536, compound

Product 1

HCID 178489193HCID 178489193, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4 g of 6-[4-(4-chlorophenyl)-5-(4-methoxyphenyl)-2-oxazolyl]hexanenitrile, twice 2 g of sodium azide and twice 1.7 g of ammonium chloride in 50 cm3 of dimethylformamide are heated according to Example 5. The product of the reaction is purified by chromatography on a column 2 cm in diameter containing 40 g of silica gel (50 to 200μ). The column is eluted, collecting 25 cm3 fractions, first with 0.2 liter of diisopropyl ether and then with 0.3 liter of ethyl acetate. The ethyl acetate eluates are concentrated to dryness and the solid residue is crystallised in 40 cm3 of ethanol. 2 g (45%) of 5-{5-[4-(4-chlorophenyl)-5-(4-methoxyphenyl)-2-oxazolyl]pentyl}tetrazole, white crystals, melting point 160° C., are obtained.

Workup

  1. customThe product of the reaction is purified by chromatography on a column 2 cm in diameter
  2. additioncontaining 40 g of silica gel (50 to 200μ)
  3. washThe column is eluted
  4. customcollecting 25 cm3 fractions
  5. concentrationThe ethyl acetate eluates are concentrated to dryness
  6. customthe solid residue is crystallised in 40 cm3 of ethanol

Sources & evidence

ORD record
ord-7b0ee57ebf904edbb75c4a740e4f414f
Source dataset
uspto-grants-1995_04
Patent number
US05403852

Reaction notes

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