Dicyclohexylcarbodiimide → HCID 21436552, compound

HRID 2397790Notes

Reaction equation

HRID 2397790 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.Cl.[NH2:17][CH2:18][C:19](O)=[O:20].[NH2:22][C:23]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:24]=1[C:25](=[N:32][CH:33]([CH3:36])[CH2:34][OH:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C)C=O.O.O1CCCC1>[NH2:17][CH2:18][C:19]([NH:22][C:23]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:24]=1[C:25](=[N:32][CH:33]([CH3:36])[CH2:34][OH:35])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:20]

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 22316Glycine HydrochlorideHCID 21436548HCID 21436548, compound

Product 1

HCID 21436552HCID 21436552, compoundYield 32.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.5g of N,N'-dicyclohexylcarbodimide in 100ml of dimethylformamide is added a solution of 2.2g of glycine hydrochloride in 2.2ml of water in a period of about 30 seconds under stirring and ice-cooling. To the reaction mixture is immediately added dropwise a solution of 3.3g of 2-[(2-amino-5-chloro-α-phenylbenzylidene)amino]propanol in 10ml of tetrahydrofuran and the mixture is stirred for further 3 hours at room temperature. After the reaction is completed, the reaction mixture is treated by the same manner as described in the Example 1 to give 1.3g of the desired product melting at 168°-172° C.

Workup

  1. temperatureice-cooling
  2. stirringthe mixture is stirred for further 3 hours at room temperature
  3. additionthe reaction mixture is treated by the same manner

Sources & evidence

ORD record
ord-32fca8d6a4434ec6b66b258b06b7b6a3
Source dataset
uspto-grants-1977_05
Patent number
US04022832

Reaction notes

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