4-Ethylbenzoic Acid → HCID 23132776, compound

HRID 1725232Notes

Reaction equation

HRID 1725232 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[CH2:11]([C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1)[CH3:12].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH:5][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:13]([CH2:11][CH3:12])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 120864-Ethylbenzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27332442,4-Difluorobenzylamine

Product 1

HCID 23132776HCID 23132776, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,4-difluorobenzylamine (3.58 g, 25.0 mmol) in methylene chloride (250 mL) were added 4-ethylbenzoic acid (3.94 g, 26.3 mmol) and DMAP (3.36 g, 27.5 mmol) followed by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.27 g, 27.5 mmol) and the reaction mixture was stirred at room temperature overnight. The resulting solution was washed with 5% HCl (3×100 mL), saturated aqueous NaHCO3 (100 mL), and brine (100 mL) and dried over Na2SO4. Concentration in vacuo afforded 6.49 g (94%) of white solid.

Workup

  1. washThe resulting solution was washed with 5% HCl (3×100 mL), saturated aqueous NaHCO3 (100 mL), and brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-5e3dcd2b8e4a4c8f9d4ba5db4cfe7cd1
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

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