1,1'-Carbonyldiimidazole → HCID 23348591, compound

HRID 1855780Notes

Reaction equation

HRID 1855780 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2].NCN1CC[CH2:17][C:16]1=[O:20].NCN1CC[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:24]1=[O:32]>C(Cl)Cl>[O:32]=[C:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:12][CH2:11][N:10]1[CH2:9][NH:8][C:1]([NH:3][CH2:4][N:5]1[CH2:6][CH2:7][CH2:17][C:16]1=[O:20])=[O:2]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 18958550HCID 18958550, compoundHCID 23348572HCID 23348572, compound

Product 1

HCID 23348591HCID 23348591, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 8.1 g (0.05 mole) of 1,1'-carbonyldiimidazole in 20 ml of methylene chloride is added, with vigorous stirring, to a solution of 5.7 g (0.05 mole) of 1-aminomethyl-2-pyrrolidinone in 20 ml of methylene chloride cooled to -70° C., whereafter 8.5 g (0.05 mole) of 1-aminomethyloctahydro-2H-azonin-2-one in 20 ml of methylene chloride are also added. After the addition, the reaction mixture is heated under reflux for 2 hours. After evaporation of the solvent under reduced pressure, the residue obtained is purified by chromatography on silica (eluent: chloroform). 5.7 g (0.0184 mole) of 1-[(octahydro-2-oxo-1H-azonin-1-yl)methyl]-3-[(2-oxopyrrolidino)methyl]-urea are thus obtained.

Workup

  1. additionare also added
  2. additionAfter the addition
  3. temperaturethe reaction mixture is heated
  4. temperatureunder reflux for 2 hours
  5. customAfter evaporation of the solvent under reduced pressure
  6. customthe residue obtained
  7. customis purified by chromatography on silica (eluent: chloroform)

Sources & evidence

ORD record
ord-584d1561918e4664920aa7b319f490ac
Source dataset
uspto-grants-1980_08
Patent number
US04216221

Reaction notes

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