Ammonium → HCID 18977010, compound

HRID 2393726Notes

Reaction equation

HRID 2393726 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[N:13]([CH2:16][CH2:17][N:18]=[N+:19]=[N-:20])=[N+:14]=[N-:15].[NH4+:21].[CH3:22][CH2:23][CH2:24][CH2:25][CH2:26]C>>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([NH:15][N:14]=[N:13][CH2:16][CH2:17][N:18]=[N:19][NH:20][C:23]2[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=2)[CH:8]=1

Participants

6

Reactant 5

HCID 223AmmoniumHCID 8058Hexane3×HCID 122863-BromopyridineHCID 61176Ethane, 1,2-diazido-HCID 178418339Butyllithium

Product 1

HCID 18977010HCID 18977010, compound

Conditions

Temperature
-60 °C

Procedure

A solution of 5 ml. of 2.5M butyllithium in hexane, diluted further with 10 ml. of hexane, was chilled to -90° C. This was treated by dropwise addition with 1.97 g (12.5 mmoles) of 3-bromopyridine in 10 ml. of hexane. The yellow slurry was stirred at -60° C. for 1 hr. and then treated by dropwise addition with 0.70 g (6.2 mmoles) of 1,2-diazidoethane. The solution remained yellow, and was stirred at room temperature overnight. The reaction mixture was then treated with ammonium buffer and the solvents were removed in vacuo. The residue was treated with 50 ml. of diethylether and 10 ml. of water overnight. The residual powder was virtually pure product in a yield of 120 mg (pale orange). The product migrated as a single spot on thin layer chromatography and the nmr and mass spectra were fully consistent with the structure.

Workup

  1. stirringwas stirred at room temperature overnight
  2. customthe solvents were removed in vacuo
  3. additionThe residue was treated with 50 ml
  4. customof water overnight

Sources & evidence

ORD record
ord-e1e77c57434443de8d10232ba5aca2ab
Source dataset
uspto-grants-1998_09
Patent number
US05808038

Reaction notes

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