Triethylamine → 57908-72-2

HRID 2071866Notes

Reaction equation

HRID 2071866 reaction equation
[C:1]([NH:5][N:6]=[C:7]([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Br:17]Br>CCCCC>[C:1]([N:5]=[N:6][C:7]([Br:17])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24408BromineHCID 11829456HCID 11829456, compound

Product 1

HCID 2141271357908-72-2

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
5 °C

Procedure

Into a solution of 25.6 grams (0.2 mole) of acetone t-butylhydrazone and 20.3 grams (0.2 mole) of triethylamine in 200 ml of pentane, cooled to 5° C in a 500 ml 4-neck round bottom flask equipped with a mechanical stirrer and thermometer, was added 31.9 grams (0.2 mole) of bromine from an addition funnel. After the addition was complete the reaction was stirred an additional 1/2 hour at 5° C, filtered to remove the triethylamine hydrobromide and the pentane evaporated from the filtrate under reduced pressure. The residue was an orange yellow liquid weighing 40 grams (96.6% crude yield). The infrared spectrum of the residue was in agreement with the structure of 2-t-butylazo-2-bromopropane.

Workup

  1. customequipped with a mechanical stirrer
  2. additionAfter the addition
  3. filtrationfiltered
  4. customto remove the triethylamine hydrobromide
  5. customthe pentane evaporated from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-68aaceef930f41aeb0e73e11faf54553
Source dataset
uspto-grants-1977_09
Patent number
US04048423

Reaction notes

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