Dimethylformamide → HCID 71238765, compound

HRID 1025409Notes

Reaction equation

HRID 1025409 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[C:20]([CH2:22][C:23](O)=[O:24])#[N:21].CN(C=O)C.CCN=C=NCCCN(C)C.Cl>O>[C:20]([CH2:22][C:23]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH:19]=2)=[CH:6][CH:7]=1)=[O:24])#[N:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9740Cyanoacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68207886HCID 68207886, compound

Product 1

HCID 71238765HCID 71238765, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 43.9 g of methyl 4-[2-(4-aminophenyl)ethyl]benzoate, 22.3 g of cyanoacetic acid, and 150 mL of DMF was added 49.5 g of EDCI/hydrochloride under ice-cooling. After stirring at room temperature for 24 hours, to the reaction mixture was added 450 mL of water at room temperature. After vigorous stirring at room temperature for 30 minutes, the precipitate was collected by filtration to obtain 54.2 g of methyl 4-(2-{4-[(cyanoacetyl)amino]phenyl}ethyl)benzoate as a white solid.

Workup

  1. temperaturecooling
  2. stirringAfter vigorous stirring at room temperature for 30 minutes
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-7ab997dfb7aa405e906e375610a86631
Source dataset
uspto-grants-2014_05
Patent number
US08729068B2

Reaction notes

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