Dicyclohexylcarbodiimide → N-[2,6-bis(1-methylethyl)phenyl]-5-decyl-2H-tetrazole-2-acetamide

HRID 2380482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2380482
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].[CH2:14]([C:24]1[N:25]=[N:26][N:27]([CH2:29][C:30](O)=[O:31])[N:28]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[CH3:12][CH:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[NH:6][C:30](=[O:31])[CH2:29][N:27]1[N:26]=[N:25][C:24]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[N:28]1)[CH3:13]

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 32484DiisopropylanilineHCID 214695295-decyl-2H-tetrazole-2-acetic acid

Produkt 1

HCID 21469460N-[2,6-bis(1-methylethyl)phenyl]-5-decyl-2H-tetrazole-2-acetamideAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2,6-diisopropyl aniline (0.97 g, 0.006 mol) and 5-decyl-2H-tetrazole-2-acetic acid (1.47 g, 0.006 mol) in 100 mL dichloromethane was cooled to 0° C. under an atmosphere of nitrogen. Solid DCC (1.19 g, 0.006 mol) was added in one portion and the resulting suspension was warmed to room temperature and stirred for 16 hours. Concentrated in vacuo and triturated the residue with diethyl ester. Filtered to remove the dicyclohexyl urea by-product. Concentrated the filtrate and triturated with hexanes to give the title compound (2.02 g, 86%) as an off-white solid, mp 108°-110° C.

Aufarbeitung

  1. concentrationConcentrated in vacuo
  2. customtriturated the residue with diethyl ester
  3. filtrationFiltered
  4. customto remove the dicyclohexyl urea by-product
  5. concentrationConcentrated the filtrate
  6. customtriturated with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e336ed24b3c1422eb8c1c233131a548b
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05366987

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