Ammonium Chloride → HCID 178420254, compound

HRID 2417832Notes

Reaction equation

HRID 2417832 reaction equation
C(CCCCC[C:8]1[N:9]=[CH:10][N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=12)#N.[N-:17]=[N+:18]=[N-:19].[Na+].[Cl-].[Li+].[Cl-].[NH4+:24]>CN(C)C=O>[NH:17]1[C:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:16]2[N:11]3[CH:10]=[N:9][CH:8]=[C:12]3[CH:13]=[CH:14][CH:15]=2)=[N:24][N:19]=[N:18]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 433294Lithium ChlorideHCID 86739620HCID 86739620, compound

Product 1

HCID 178420254HCID 178420254, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(5-cyanopentyl-imidazo[1,5-a]pyridine (5.26 g) in 16 ml of dry dimethylformamide is heated at 120° for 15 hours with sodium azide (2.15 g), lithium chloride (0.2 g) and ammonium chloride (1.80 g). After cooling and filtering, the solvent is evaporated and the residue is dissolved in 50 ml of water, extracted with 25 ml of ethyl acetate and brought to pH=5 with concentrated sulfuric acid. The precipitated solid is filtered, washed with water and dried to yield 5-[5-(5-tetrazolyl)pentyl]imidazo[1,5-a]pyridine, m.p. 149°-150°. The mono-hydrochloride salt has m.p. 188°-190°.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltering
  3. customthe solvent is evaporated
  4. dissolutionthe residue is dissolved in 50 ml of water
  5. extractionextracted with 25 ml of ethyl acetate
  6. filtrationThe precipitated solid is filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-5a978a769df64aa1afdfcecbd3d54c63
Source dataset
uspto-grants-1984_09
Patent number
US04470986

Reaction notes

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