Ammonium Chloride → HCID 178422056, compound

HRID 1633143Notes

Reaction equation

HRID 1633143 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[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)#[N:2].[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+].[Cl-].[Li+]>CN(C=O)C>[NH:23]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[C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[N:2][N:25]=[N:24]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 433294Lithium ChlorideHCID 13362115HCID 13362115, compound

Product 1

HCID 178422056HCID 178422056, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 578 mg of 1-(4-cyanobutyl)-3-methyl-2-(3-pyridyl)indole, 173 mg of sodium azide, 142 mg of ammonium chloride and 5 mg of lithium chloride in 2 ml of DMF 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 3 N NaOH, the solution is washed with ether to remove unreacted nitrile. The aqueous phase is adjusted to pH 5-6 with 2 N HCl and extracted with ether. The ether extract is washed with water, dried over MgSO4 and concentrated in vacuo. The solid residue is slurried in petroleum ether and collected to give 1-[4-(5-tetrazolyl)-butyl]-3-methyl-2-(3-pyridyl)indole, m.p. 177°-179°.

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 ether
  8. extractionThe ether extract
  9. washis washed with water
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated in vacuo
  12. customcollected

Sources & evidence

ORD record
ord-f7c75ec7ee4b4477ae9defba23108492
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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