1-Hydroxybenzotriazole → N-[2-(4-chlorophenoxy)ethyl]-3-(3,4-dimethoxybenzamido)-4-methylbenzamide

HRID 502033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502033
Cl.CN(C)CCCN=C=NCC.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[C:18]([NH:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[CH3:30])[C:24]([OH:26])=O)=[O:19].[Cl:36][C:37]1[CH:46]=[CH:45][C:40]([O:41][CH2:42][CH2:43][NH2:44])=[CH:39][CH:38]=1.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:36][C:37]1[CH:46]=[CH:45][C:40]([O:41][CH2:42][CH2:43][NH:44][C:24](=[O:26])[C:23]2[CH:27]=[CH:28][C:29]([CH3:30])=[C:21]([NH:20][C:18](=[O:19])[C:17]3[CH:31]=[CH:32][C:33]([O:34][CH3:35])=[C:15]([O:14][CH3:13])[CH:16]=3)[CH:22]=2)=[CH:39][CH:38]=1

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27941912-(4-Chlorophenoxy)ethylamineHCID 36001793-[(3,4-Dimethoxybenzoyl)amino]-4-methylbenzoic acid

Produkt 1

HCID 22636102N-[2-(4-chlorophenoxy)ethyl]-3-(3,4-dimethoxybenzamido)-4-methylbenzamideAusbeute 67,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.095 g) in methylene chloride (5 ml) was added to a stirred mixture of 3-(3,4-dimethoxybenzamido)-4-methylbenzoic acid (0.157 g), 2-(4-chlorophenoxy)ethylamine (C. Chim. Ther., 1973, 8, 259; 0.086 g), 4-dimethylaminopyridine (0.007 g), 1-hydroxybenzotriazole (0.074 g) and methylene chloride (5 ml). The resultant mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organic phase was washed with an aqueous citric acid solution, dried over magnesium sulphate and evaporated. There was thus obtained the title compound as a solid (0.158 g); Mass Spectrum: M+H+ 469.

Aufarbeitung

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate
  3. washThe organic phase was washed with an aqueous citric acid solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d534d7fcd7fa4f299534f054646de1cd
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772432B2

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