Ammonium → HCID 18977005, compound

HRID 2393724Notes

Reaction equation

HRID 2393724 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[N:8]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]=[N+:16]=[N-:17])=[N+:9]=[N-:10].[NH4+:18]>CCCCC.CCCCCC>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:10][N:9]=[N:8][CH2:11][CH2:12][CH2:13][CH2:14][N:15]=[N:16][NH:17][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:18]=1

Participants

6

Reactant 3

HCID 223AmmoniumHCID 79732-BromopyridineHCID 136209641,4-Diazidobutane

Product 1

HCID 18977005HCID 18977005, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 3.95 g (25 mmoles) of 2-bromopyridine in 20 ml of dry pentane was added dropwise to 10 ml. of 2.5M butylithium in hexane at -78° C. To the resulting yellow slurry was added dropwise with stirring 1.75 g (12.5 mmoles) of 1,4-diazidobutane in 10 ml. of pentane. Stirring was continued for 2 hr. at -78° and then the reaction mixture was allowed to warm to room temperature. The reaction mixture was treated with 60 ml. of ammonium buffer which caused a precipitate to appear after the reaction was cooled to -78° C. The solid was filtered off. It was poorly soluble in common solvents such as halomethanes, acetone, methanol and water. It was sparingly soluble in dimethylsulfoxide. The yield was 2.3 g., m.p. 133-136. Spectroscopic data were consistent with the structure.

Workup

  1. customat -78° C
  2. additionTo the resulting yellow slurry was added dropwise
  3. customat -78°
  4. additionThe reaction mixture was treated with 60 ml
  5. temperaturewas cooled to -78° C
  6. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-2593938d6c904d25a07ee2dfcc429eb7
Source dataset
uspto-grants-1998_09
Patent number
US05808038

Reaction notes

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