Hydrochloric Acid → HCID 71238765, compound

HRID 2175989Notes

Reaction equation

HRID 2175989 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].CCN=C=NCCCN(C)C.Cl>O.CN(C=O)C>[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9740Cyanoacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68207886HCID 68207886, compound

Product 1

HCID 71238765HCID 71238765, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

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 WSC.hydrochloride under ice cooling. After the reaction mixture was stirred for 24 hours at room temperature, 450 mL of water was added thereto at room temperature, followed by stirring for 30 minutes at room temperature. Thereafter, the precipitate was collected by filtration, thereby obtaining 54.2 g of methyl 4-(2-{4-[(cyanoacetyl)amino]phenyl}ethyl)benzoate.

Workup

  1. customat room temperature
  2. stirringby stirring for 30 minutes at room temperature
  3. filtrationThereafter, the precipitate was collected by filtration

Sources & evidence

ORD record
ord-fbf8e5128b054b959480e7b402345994
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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