Ammonium → HCID 18977000, compound

HRID 2393725Notes

Reaction equation

HRID 2393725 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=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>O1CCCC1.N1C=CC=CC=1>[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[NH:15][N:14]=[N:13][CH2:16][CH2:17][N:18]=[N:19][NH:20][C:26]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1

Participants

8

Reactant 5

HCID 223AmmoniumHCID 79732-BromopyridineHCID 8058HexaneHCID 61176Ethane, 1,2-diazido-HCID 178418339Butyllithium

Product 1

HCID 18977000HCID 18977000, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of butyllithium in hexane (5 ml., 2.5M) was dissolved in 10 ml. of tetrahydrofuran and cooled to -78° C. To this was added dropwise with stirring a solution of 1.98 g (12.5 mmoles) of 2-bromopyridine in 10 ml. of tetrahydrofuran. The dark yellow solution of the pyridine anion was mixed with a solution of 0.70 g (6.2 mmoles) of 1,2-diazidoethane in 10 ml. of tetrahydrofuran at -78° C. After 1 hr. of stirring the dark green solution was treated with 10 ml. of ammonium buffer. The color changed to yellow. The organic solvent was removed in vacuo, and the precipitate was isolated by filtration and washed with copious quantities of diethylether. The powdery material was finally dried under high vacuum. The yield was 770 mg. This material was not soluble in most solvents, except dimethylsulfoxide. It did not have a sharp melting point since decomposition began before it was reached (rapid above 100° C.). The spectra, however, were fully consistent with the structure.

Workup

  1. additionTo this was added dropwise
  2. customat -78° C
  3. additionwas treated with 10 ml
  4. customThe organic solvent was removed in vacuo
  5. customthe precipitate was isolated by filtration
  6. washwashed with copious quantities of diethylether
  7. customThe powdery material was finally dried under high vacuum
  8. custom(rapid above 100° C.)

Sources & evidence

ORD record
ord-2e0331a1cb964a438e4af4978ee39f49
Source dataset
uspto-grants-1998_09
Patent number
US05808038

Reaction notes

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