Dimethylformamide → HCID 71238730, compound

HRID 926022Notes

Reaction equation

HRID 926022 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-bdf61bc35942492f983b9f092e0cc77c
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Reaction notes

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