Ammonium Chloride → HCID 21279726, compound

HRID 2291319Notes

Reaction equation

HRID 2291319 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH2:10][C:11]2C=CC=[CH:13][CH:12]=2)[N:4]=1.[NH4+:17].[Cl-]>N>[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH2:10][CH2:11][CH2:12][C:13]#[N:17])[N:4]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 21279834HCID 21279834, compound

Product 1

HCID 21279726HCID 21279726, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of 2-amino-6-benzylthiopyridine hydrochloride (47.2 g.) in liquid NH3 (700 ml.) was stirred while Na (17.0 g.) was added in small portions. When the addition was complete NH4Cl (21.9 g.) was added and then the mixture was evaporated to dryness. The residue was dissolved in a mixture of EtOH (100 ml.) and H2O (100 ml.) and the mixture treated with 4-bromobutyronitrile (23 ml.) and stirred at room temperature for 18 hours. The solution was evaporated to dryness and the residue was partitioned between 2N aqueous HCl and ether. The aqueous phase was basified with 10N aqueous NaOH and extracted with EtOAc. The extract was dried over Na2SO4 and evaporated to dryness to give 4-(2-aminopyrid-6-ylthio)butyronitrile (36.1 g.) which was used without further purification.

Workup

  1. additionwas added in small portions
  2. additionWhen the addition
  3. additionwas added
  4. customthe mixture was evaporated to dryness
  5. dissolutionThe residue was dissolved in a mixture of EtOH (100 ml.) and H2O (100 ml.)
  6. additionthe mixture treated with 4-bromobutyronitrile (23 ml.)
  7. customThe solution was evaporated to dryness
  8. customthe residue was partitioned between 2N aqueous HCl and ether
  9. extractionextracted with EtOAc
  10. dry with materialThe extract was dried over Na2SO4
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-acb2f8a7850441d2ad9328b3876dd154
Source dataset
uspto-grants-1989_01
Patent number
US04795755

Reaction notes

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