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Methylamine → 6-bromo-N-methyl-2-naphtamide

HRID 724202
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 724202
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=O)[CH:6]=[CH:5]2.Cl.[CH2:16]([N:18]=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.CN>CN(C)C=O.C1COCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH:18][CH3:16])=[O:14])[CH:6]=[CH:5]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 45498526-Bromo-2-naphthalenecarboxylic acid

Produkt 1

HCID 21879628
6-bromo-N-methyl-2-naphtamide
Ausbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-Bromo-2-naphthoic acid (60.26 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (55.21 g) and 1-hydroxy-1H-benzotriazole monohydrate (44.1 g) were dissolved in dimethylformamide (960 ml) under an argon atmosphere. N-Ethyldiisopropylamine (37.23 g) was added with stirring under ice-cooling. A solution (2M; 192 ml) of methylamine in THF was added and the mixture was stirred at room temperature for 18 h. The reaction mixture was poured into water (8 L) with stirring and the precipitate was collected by filtration. The precipitate was washed successively with water and diisopropyl ether, and dried in the presence of phosphorus pentaoxide at 70° C. to give the title compound (60.6 g) as a crystalline powder.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 18 h
  3. stirringwith stirring
  4. filtrationthe precipitate was collected by filtration
  5. washThe precipitate was washed successively with water and diisopropyl ether
  6. dry with materialdried in the presence of phosphorus pentaoxide at 70° C.

Quellen und Nachweise

ORD-Eintrag
ord-4d3f1c0be4c248248a53381ce6b49229
Quelldatensatz
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07141598B2

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