Lithium azide → HCID 11994354, compound

HRID 1741482Notes

Reaction equation

HRID 1741482 reaction equation
CS(O[CH2:6][C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1C(=O)C(F)(F)F)(=O)=O.[N-:18]=[N+:19]=[N-:20].[Li+]>CN(C=O)C>[N:18]([CH2:6][C@@H:7]1[CH2:11][CH2:10][CH2:9][NH:8]1)=[N+:19]=[N-:20]

Participants

4

Reactant 2

HCID 88163Lithium azideHCID 18660145HCID 18660145, compound

Product 1

HCID 11994354HCID 11994354, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a flask protected by a safety screen, a solution of the product of step B (12.27 g, 0.042 mmol) and lithium azide (2.47 g, 0.051 mmol) in DMF (30 ml) was stirred at 45° C. for 18 hr. The solvent was evaporated in vacuo and the residue triturated with EtOAc (100 ml) and filtered. The filtrate was evaporated in vacuo and the residue dissolved in MeOH (255 ml) which was saturated with gaseous ammonia at 0° C. and then stirred at room temperature for 72 hr. The solvent was removed by distillation in vacuo to afford the title compound as an oil.

Workup

  1. customIn a flask protected by a safety screen
  2. customThe solvent was evaporated in vacuo
  3. customthe residue triturated with EtOAc (100 ml)
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. dissolutionthe residue dissolved in MeOH (255 ml) which
  7. customwas saturated with gaseous ammonia at 0° C.
  8. customThe solvent was removed by distillation in vacuo

Sources & evidence

ORD record
ord-6cffc8195cad4dce86b7aee1ac91910d
Source dataset
uspto-grants-1999_10
Patent number
US05972984

Reaction notes

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