N-Methylethylamine → N-[2-(3-cyanophenoxy)ethyl]-4-(N-methyl-N-ethylcarbamoyl)benzamide

HRID 747665Notes

Reaction equation

HRID 747665 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][NH:9][C:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)=[O:11])#[N:2].[CH2:24]([NH:26][CH3:27])[CH3:25].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>Cl>[C:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[C:12]1[CH:13]=[CH:14][C:15]([C:16](=[O:18])[N:26]([CH3:27])[CH2:24][CH3:25])=[CH:19][CH:20]=1)#[N:2]

Participants

6

Reactant 4

HCID 12219N-MethylethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 688315184-[N-[2-(3-cyanophenoxy)ethyl]carbamoyl]benzoic acid

Product 1

HCID 68830104N-[2-(3-cyanophenoxy)ethyl]-4-(N-methyl-N-ethylcarbamoyl)benzamide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

258 mg (0.83 mmol) of 4-[N-[2-(3-cyanophenoxy)ethyl]carbamoyl]benzoic acid, 53 mg (0.9 mmol) of N-ethyl-N-methylamine, 129 mg (0.83 mmol) of 1-hydroxybenzotriazole (hydrous, 87%) and 159 mg (0.83 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were stirred in 10 ml of dichloro ee at room temperature overnight. The resultant mixture was diluted with 1 N hydrochloric acid. After the extraction with dichloromethane, the organic layer was washed with 1 N aqueous sodium hydroxide solution and then with saturated aqueous NaCl solution and dried over anhydrous magnesium-sulfate. The solvent was evaporated to obtain the title compound.

Workup

  1. extractionAfter the extraction with dichloromethane
  2. washthe organic layer was washed with 1 N aqueous sodium hydroxide solution
  3. dry with materialwith saturated aqueous NaCl solution and dried over anhydrous magnesium-sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e3b794dff0b24d9bb6be2ed2c9b71621
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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