Nonylamine → 5-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-N-nonyl-benzamide

HRID 1270581

Reaktionsgleichung

Reaktionsgleichung von HRID 1270581
[Cl:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([Cl:23])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:14][CH3:15])=[C:9]([CH:13]=1)[C:10](O)=[O:11].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH2:47]([NH2:56])[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]>C(Cl)Cl>[Cl:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([Cl:23])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:14][CH3:15])=[C:9]([CH:13]=1)[C:10]([NH:56][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[O:11]

Komponenten

6

Edukt 4

HCID 16215NonylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 223449015-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-benzoic acid

Produkt 1

HCID 223448745-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-N-nonyl-benzamideAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 5-(2,6-dichloro-4-nitro-phenoxy)-2-methoxy-benzoic acid (150 mg, 0.42 mmol) in CH2Cl2 (2 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (84 mg, 0.44 mmol) and 1-hydroxybenzotriazole hydrate (77 mg, 0.50 mmol) with stirring at RT. To the resulting yellow solution was added nonylamine (154 μl, 0.84 mmol) at RT. The resulting mixture was stirred 2 h at RT then solvent removed under a dry nitrogen stream. The residue was purified by preparative TLC (5% Et2O, 45% hexanes, 50% CH2Cl2) to give the title compound of Step C (173 mg). MS (APCI+) Calc.: 482.1, Found: 483.2 (M+1).

Aufarbeitung

  1. stirringThe resulting mixture was stirred 2 h at RT
  2. customsolvent removed under a dry nitrogen
  3. customThe residue was purified by preparative TLC (5% Et2O, 45% hexanes, 50% CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-4012ac7ae1774f49a40a72200636673b
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202275B2

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