1,1'-Carbonyldiimidazole → HCID 67424696, compound
Reaction equation
[CH:1]1N=C[N:3]([C:6]([N:8]2[CH:12]=[N:11][CH:10]=[CH:9]2)=[O:7])[CH:2]=1.[Cl-].[CH3:14][C:15](=[CH2:22])[C:16]([O:18]CC[NH3+])=[O:17]>O1CCCC1>[N:8]1([C:6]([NH:3][CH2:2][CH2:1][O:18][C:16](=[O:17])[C:15]([CH3:22])=[CH2:14])=[O:7])[CH:9]=[CH:10][N:11]=[CH:12]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 17 °C
Procedure
25.4 g (0.17 mole, >97% FLUKA) CDI were suspended in about 150 ml THF (tetrahydro furane) at room temperature. Upon partial dissolution the suspension was cooled down to about 17° C. After about 30 min stirring 25.9 g (0.16 mole) 2-(2-Methyl-acryloyloxy)-ethyl-ammonium chloride were added to the mixture under cooling on ice in several portion during about 1 h keeping the reaction mixture at about 23° C. A yellow suspension was obtained. After about 3 h of stirring at about 23° C. the suspension was filtrated. The filter cake was washed with THF. To the clear yellow filtrate about 300 mg phenothiazine were added. Solvent was evaporated. A clear orange viscous resin was obtained (containing traces of residual solvent). Yield was quantitative, 1H NMR indicates the desired product.
Workup
- dissolutionUpon partial dissolution the suspension
- additionwere added to the mixture
- temperatureunder cooling on ice in several portion during about 1 h
- customat about 23° C
- customA yellow suspension was obtained
- filtrationwas filtrated
- washThe filter cake was washed with THF
- additionTo the clear yellow filtrate about 300 mg phenothiazine were added
- customSolvent was evaporated
- customA clear orange viscous resin was obtained
- addition(containing traces of residual solvent)
- customYield
Sources & evidence
- ORD record
- ord-863a83a9a09b46e1862d0421b12f5c77
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006480B2
Reaction notes
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