Diisopropylcarbodiimide → HCID 53925756, compound

HRID 1580632Notes

Reaction equation

HRID 1580632 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]1=[NH:16].[CH:17]([N:20]=[C:21]=[N:22][CH:23]([CH3:25])[CH3:24])([CH3:19])[CH3:18]>C(O)(C)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]1=[N:16][C:21]([NH:22][CH:23]([CH3:25])[CH3:24])=[N:20][CH:17]([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 12734DiisopropylcarbodiimideHCID 12255204HCID 12255204, compound

Product 1

HCID 53925756HCID 53925756, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 1-[2-(2-bromophenyl)ethyl]-2-iminopyridine (2.77 g, 0.01 mole) and diisopropylcarbodiimide (1.05 g, 0.012 mole) in 30 ml of t-butanol is heated at reflux in a nitrogen atmosphere for 24 hours. The solution is cooled to room temperature and concentrated in vacuo to give a solid. This is recrystallized from 50 ml of hexane to yield a semi-solid, after cooling to -30°C. Recrystallization of this material from 70 ml of hexane yields 1.83 g of the title compound which sinters at 119°C and melts at 125°-128°C.

Workup

  1. temperatureat reflux in a nitrogen atmosphere for 24 hours
  2. concentrationconcentrated in vacuo
  3. customto give a solid
  4. customThis is recrystallized from 50 ml of hexane
  5. customto yield a semi-solid
  6. temperatureafter cooling to -30°C
  7. customRecrystallization of this material from 70 ml of hexane

Sources & evidence

ORD record
ord-7ff8c22ef6414fd3a0999d016c3b34e6
Source dataset
uspto-grants-1976_01
Patent number
US03933836

Reaction notes

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