1-Heptadecanol → 4-Heptadecyloxycarbonyl-2-nitroaniline

HRID 728406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 728406
[N+:1]([C:4]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[CH2:14](O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].CN(C1C=CC=CN=1)C>ClCCl>[N+:1]([C:4]1[CH:10]=[C:9]([C:11]([O:13][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])=[O:12])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 150761-HeptadecanolHCID 218852-DimethylaminopyridineHCID 74115Benzoic acid, 4-amino-3-nitro-

Produkt 1

HCID 198239524-Heptadecyloxycarbonyl-2-nitroaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 2-nitro-4-carboxyaniline (0.52 g), heptadecanol (0.7 g) and dimethylaminopyridine (20 mg) in dichloromethane (20 ml) was prepared and dicyclohexyldicarbodiimide (0.62 g) was added. The mixture was stirred for 48 hours and filtered. After separating between chloroform and 3% caustic soda solution the organic phase was washed with water, dried with magnesium sulphate and the solvent removed to leave a yellow solid. The solid was purified by chromatography to give a yellow solid which was recrystallised from 50:50 chloroform-hexane (yield: 0.85 g, m.p. 103°-105° C.).

Aufarbeitung

  1. customwas prepared
  2. filtrationfiltered
  3. customAfter separating between chloroform and 3% caustic soda solution the organic phase
  4. washwas washed with water
  5. dry with materialdried with magnesium sulphate
  6. customthe solvent removed
  7. customto leave a yellow solid
  8. customThe solid was purified by chromatography
  9. customto give a yellow solid which
  10. customwas recrystallised from 50:50 chloroform-hexane (yield: 0.85 g, m.p. 103°-105° C.)

Quellen und Nachweise

ORD-Eintrag
ord-5f8ed30fdc3d4ee4b3f7cfd705ea5317
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05047516

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