Dicyclohexylcarbodiimide → HCID 54107370, compound

HRID 1580634Notes

Reaction equation

HRID 1580634 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]1([N:23]=[C:24]=[N:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C(O)(C)(C)C.CCCCCC>[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:24]([NH:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[N:23][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 12255204HCID 12255204, compound

Product 1

HCID 54107370HCID 54107370, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8058HexaneSolvent

Procedure

A solution of 1-[2-(2-bromophenyl)ethyl]-2-iminopyridine (2.77 g, 0.01 mole) and dicyclohexylcarbodiimide (2.06 g, 0.01 mole) in 30 ml of t-butanol is heated at reflux for 21.5 hours under a nitrogen blanket. The solution is cooled to room temperature and diluted with 60 ml of hexane. The diluted solution is cooled and scratched in a dry ice bath to induce crystallization. The mixture is allowed to warm to room temperature and is filtered to give 0.58 g of material which sinters at 121°C and melts at 125°-129°C. The filtrate is concentrated in vacuo and the residual oil is cooled in an ice bath and scratched under 40 ml of hexane to give 1.32 g of material which sinters at 100°C and melts at 108°-110°C. The two batches of material are combined and dissolved in a boiling solution of 60 ml of cyclohexane and 60 ml hexane and filtered. The solution is cooled for several hours at -30°C, filtered and washed with cooled hexane to yield 1.33 g of the title compound, melting point 127°-129.5°C.

Workup

  1. temperatureat reflux for 21.5 hours under a nitrogen blanket
  2. temperatureThe diluted solution is cooled
  3. customscratched in a dry ice bath
  4. customcrystallization
  5. temperatureto warm to room temperature
  6. filtrationis filtered

Sources & evidence

ORD record
ord-94582de095c4499b81a88d568eadaaaf
Source dataset
uspto-grants-1976_01
Patent number
US03933836

Reaction notes

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