Triethylamine → (E)-1-tert-Butyl-2-(2-chloro-4-methylpentan-2-yl)diazene

HRID 1579171Notes

Reaction equation

[C:1]([NH:5][N:6]=[C:7]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:20]Cl>CCCCC>[C:1]([N:5]=[N:6][C:7]([Cl:20])([CH2:9][CH:10]([CH3:12])[CH3:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -15 °C

Procedure

Into a 5 liter, 4-neck round bottom flask equipped with a low temperature thermometer, a chlorine inlet tube, a mechanical stirrer, and a gas exit tube protected from the atmosphere with a CaCl2 tube, was added 510 grams (3.0 moles) of methyl isobutyl ketone t-butylhydrazone, 303.6 grams (3.0 moles) of triethylamine and 2400 ml of pentane. The contents were cooled to -15°C with a dry ice-isopropanol bath. Then with rapid stirring 213 grams (3.0 moles) of chlorine were passed into the reaction mixture as fast as it was possible to control the temperature at 5°C or below. After all of the chlorine had been added the reaction temperature was adjusted to -5°C to 0°C and the reaction mixture filtered to remove the triethylamine hydrochloride. The triethylamine hydrochloride filter cake was washed with fresh pentane and the filtrate added to the original pentane solution.

Workup

customInto a 5 liter, 4-neck round bottom flask equipped with a low temperature thermometer, a chlorine inlet tube, a mechanical stirrer, and a gas exit tube
customprotected from the atmosphere with a CaCl2 tube
customat 5°C or below
customwas adjusted to -5°C to 0°C
filtrationthe reaction mixture filtered
customto remove the triethylamine hydrochloride
filtrationThe triethylamine hydrochloride filter cake
washwas washed with fresh pentane
additionthe filtrate added to the original pentane solution

Sources & evidence

ORD record: ord-035d824f8f2f4b7db35eb114d24fb010
Source dataset: uspto-grants-1976_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03931143

Reaction notes

Loading…