Ammonium Chloride → HCID 178420204, compound

HRID 280232Notes

Reaction equation

HRID 280232 reaction equation
[C:1]([CH2:3][C:4]1[CH:20]=[CH:19][C:7]([CH2:8][CH2:9][C:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)#[N:2].[N-:21]=[N+:22]=[N-:23].[Na+].[Cl-].[Li+].[Cl-].[NH4+]>CN(C)C=O>[NH:21]1[C:1]([CH2:3][C:4]2[CH:20]=[CH:19][C:7]([CH2:8][CH2:9][C:10]3[N:15]4[CH:16]=[N:17][CH:18]=[C:14]4[CH:13]=[CH:12][CH:11]=3)=[CH:6][CH:5]=2)=[N:2][N:23]=[N:22]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 433294Lithium ChlorideHCID 23321853HCID 23321853, compound

Product 1

HCID 178420204HCID 178420204, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-[p-(cyanomethyl)phenethyl]-imidazo[1,5-a]pyridine (6.0 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-[p-(5-tetrazolylmethyl)phenethyl]-imidazo[1,5-a]pyridine.

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-048fa4e424324b6483d2ce6c91588ef7
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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