O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → N-(4-Chloro-3-nitrobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

HRID 1258664Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258664
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[F:23][C:24]([F:32])([F:31])[C:25]1([C:28](O)=[O:29])[CH2:27][CH2:26]1.[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][C:35]=1[N+:42]([O-:44])=[O:43]>C1COCC1>[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH:39][C:28]([C:25]2([C:24]([F:32])([F:31])[F:23])[CH2:27][CH2:26]2)=[O:29])=[CH:36][C:35]=1[N+:42]([O-:44])=[O:43]

Komponenten

5

Edukt 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27783061-(Trifluoromethyl)cyclopropane-1-carboxylic acidHCID 18796740(4-Chloro-3-nitrophenyl)methanamine

Produkt 1

HCID 59529820N-(4-Chloro-3-nitrobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

TBTU (0.44 g, 1.4 mmol) and TEA (0.43 mL, 3.1 mmol) were added to 1-trifluoromethyl-cyclopropanecarboxylic acid (0.19 g, 1.2 mmol) in THF (5 mL). After 10 min at rt 4-chloro-3-nitro-benzylamine (0.23 g, 1.2 mmol) was added to the reaction mixture and stirring was continued overnight. The mixture was concentrated, diluted with EtOAc and washed with sat.aq. NaHCO3-solution, water and brine. The organic layer was dried over Na2SO4 and concentrated to give the subtitle compound.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with sat.aq
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dc1932b53c6f4cc3becb0ae023112c59
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466186B2

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