Ammonium Chloride → HCID 178429810, compound

HRID 1719396Notes

Reaction equation

HRID 1719396 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH3:16])=[C:8]1[N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)#[N:2].[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+].[Cl-].[Li+]>CN(C)C=O>[NH:22]1[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH3:16])=[C:8]2[N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)=[N:2][N:24]=[N:23]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 433294Lithium ChlorideHCID 202681831-(4-Cyanobutyl)-3-methyl-2-(1-imidazolyl)indole

Product 1

HCID 178429810HCID 178429810, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 600 mg of 1-(4-cyanobutyl)-3-methyl-2-(1-imidazolyl)indole, 173 mg of sodium azide, 142 mg of ammonium chloride and 5 mg of lithium chloride in 2 ml of dimethylformamide is heated at 120° overnight. After cooling the mixture is filtered and the filtrate diluted with ca. 25 ml of water. After the pH is adjusted to 10-11 with 3N NaOH, the solution is washed with ether to remove unreacted nitrile. The aqueous phase is adjusted to pH 5-6 with 2N HCl and extracted with ethylacetate. The extract is washed with water, dried over magnesium sulfate and concentrated in vacuo. The solid residue is slurried in petroleum ether and collected to give 1-[4-(5-tetrazolyl)-butyl]-3-methyl-2-(1-imidazolyl)indole.

Workup

  1. temperatureis heated at 120° overnight
  2. temperatureAfter cooling the mixture
  3. filtrationis filtered
  4. additionthe filtrate diluted with ca. 25 ml of water
  5. washthe solution is washed with ether
  6. customto remove unreacted nitrile
  7. extractionextracted with ethylacetate
  8. washThe extract is washed with water
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customcollected

Sources & evidence

ORD record
ord-5baa1e663170493ba30444017447bff9
Source dataset
uspto-grants-1985_09
Patent number
US04539410

Reaction notes

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