1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 10385550, compound

HRID 1242885Notes

Reaction equation

HRID 1242885 reaction equation
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH2:26].[C:28]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:33]=[CH:32][C:31]([C:34]([NH:36][C:37]2[CH:45]=[CH:44][C:40]([C:41]([O-])=[O:42])=[CH:39][CH:38]=2)=[O:35])=[CH:30][CH:29]=1>C1COCC1.C(#N)C.C(OCC)(=O)C.O.C(N(CC)CC)C>[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH:26][C:41]([C:40]1[CH:39]=[CH:38][C:37]([NH:36][C:34]([C:31]2[CH:32]=[CH:33][C:28]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)=[CH:29][CH:30]=2)=[O:35])=[CH:45][CH:44]=1)=[O:42]

Participants

10

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 7040114HCID 7040114, compound

Product 1

HCID 10385550HCID 10385550, compoundYield 25.3%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

WSC (0.248 g), HOBt (0.156 g), N,N-dimethyl ethylenediamine (0.097 g) and triethylamine (0.21 ml) were added to a mixed solution of 4-(4-biphenylylcarbonylamino)benzoate (0.323 g) in THF (15 ml) and acetonitrile (15 ml). After stirring at room temperature for 18 hours, water was added to the reaction mixture, and extraction was conducted using ethyl acetate. The organic layer was washed with 10% aqueous potassium carbonate and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was recrystallized using methanol/diethyl ether to give the titled compound (0.100 g).

Workup

  1. washThe organic layer was washed with 10% aqueous potassium carbonate and saturated aqueous sodium chloride solution
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was recrystallized

Sources & evidence

ORD record
ord-fc5eddb1212c45ee9373ad34bd861204
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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