Dimethylformamide → HCID 71238730, compound

HRID 1025410Notes

Reaction equation

HRID 1025410 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[C:21]([CH2:23][C:24](O)=[O:25])#[N:22].CN(C=O)C.CCN=C=NCCCN(C)C.Cl>O>[C:21]([CH2:23][C:24]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=2)=[CH:6][CH:7]=1)=[O:25])#[N:22]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9740Cyanoacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68207867Benzoic acid, 4-[3-(4-aminophenyl)propyl]-, methyl ester

Product 1

HCID 71238730HCID 71238730, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 16.0 g of methyl 4-[3-(4-aminophenyl)propyl]benzoate, 7.70 g of cyanoacetic acid, and 50 mL of DMF was added 17.1 g of EDCI/hydrochloride under ice-cooling. After stirring at room temperature for 18 hours, to the reaction mixture was added 200 mL of water at room temperature. After vigorous stirring at room temperature for 30 minutes, the precipitate was collected by filtration to obtain 19.3 g of methyl 4-(3-{4-[(cyanoacetyl)amino]phenyl}propyl)benzoate as a beige 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-0c6bed5f93e94881a458abbc2d498297
Source dataset
uspto-grants-2014_05
Patent number
US08729068B2

Reaction notes

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