Ammonium Chloride → HCID 178478082, compound

HRID 2417830Notes

Reaction equation

HRID 2417830 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:12]2[CH:13]=[N:14][CH:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1)#[N:2].[N-:16]=[N+:17]=[N-:18].[Na+].[Cl-:20].[NH4+].[Cl-].[Li+]>CN(C)C=O>[ClH:20].[NH:16]1[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]2[N:12]3[CH:13]=[N:14][CH:15]=[C:11]3[CH:10]=[CH:9][CH:8]=2)=[N:2][N:18]=[N:17]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 433294Lithium ChlorideHCID 132061415-(4-Cyanobutyl)-imidazo[1,5-a]pyridine

Product 1

HCID 178478082HCID 178478082, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(4-cyanobutyl)-imidazo[1,5-a]pyridine (4.0 g), sodium azide (1.88 g), ammonium chloride (1.57 g) and lithium chloride (10 mole %) in 14 ml of dry dimethylformamide is heated at 125° for 17 hours. The reaction mixture is cooled, filtered and evaporated to a residual oil which is redissolved in 50 ml of water and extracted with ethyl acetate (50 ml). The aqueous phase is adjusted to pH=2 and extracted with ethyl acetate and then adjusted to pH=5. The resulting solid is collected by filtration and converted to its hydrochloride salt which is recrystallized from acetone/methanol to yield 5-[4-(5-tetrazolyl)butyl]-imidazo[1,5-a]pyridine monohydrochloride, m.p. 159°-161°.

Workup

  1. temperatureis heated at 125° for 17 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. customevaporated to a residual oil which
  5. dissolutionis redissolved in 50 ml of water
  6. extractionextracted with ethyl acetate (50 ml)
  7. extractionextracted with ethyl acetate
  8. filtrationThe resulting solid is collected by filtration
  9. customis recrystallized from acetone/methanol

Sources & evidence

ORD record
ord-f75f80bdcc994839ba71c3aa142bcd88
Source dataset
uspto-grants-1984_09
Patent number
US04470986

Reaction notes

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