Dimethylformamide → Methyl 4-(7-(2-ethylbutylcarbamoyl)naphth-1-ylmethyl)-3-methoxybenzoate

HRID 2371798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2371798
[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[C:11]2[CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=2[O:25][CH3:26])=[CH:6][CH:5]=1)(O)=[O:2].Cl.CN(C)CCCN=C=NCC.[CH2:39]([CH:41]([CH2:44][CH3:45])[CH2:42][NH2:43])[CH3:40].CN(C)C=O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:39]([CH:41]([CH2:44][CH3:45])[CH2:42][NH:43][C:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[C:11]2[CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=2[O:25][CH3:26])=[CH:6][CH:5]=1)=[O:2])[CH3:40]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 120492-Ethyl butylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19906397HCID 19906397, Verbindung

Produkt 1

HCID 19906363Methyl 4-(7-(2-ethylbutylcarbamoyl)naphth-1-ylmethyl)-3-methoxybenzoateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of methyl 4-(7-carboxynaphth-1-ylmethyl)-3-methoxybenzoate (342 mg), 4-dimethylaminopyridine (358 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (560 mg), and 2-ethylbutylamine (198 mg), was dissolved in 3:1 methylene chloride:dimethylformamide (distilled over CaH2) (4 ml) and stirred for 18 h. Methylene chloride was added and the solution was washed (1N hydrochloric acid, brine), dried (MgSO4) and evaporated to give a yellow foam. Recrystallization from 1:2 methylene chloride:hexane (30 ml) gave methyl 4-[7-(2-ethylbutylcarbamoyl)naphth-1-ylmethyl]-3-methoxybenzoate (326 mg, 77%) as a colorless solid; mp 129.5°-130.5° C.

Aufarbeitung

  1. washthe solution was washed (1N hydrochloric acid, brine)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customto give a yellow foam
  5. customRecrystallization from 1:2 methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-35ef7378b34a4509bc341e7ce045b1c5
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05095038

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