3,4-Bis(benzyloxy)-5-nitrobenzoic acid → [(Z)-[amino-[2-(trifluoromethyl)-3-pyridinyl]methylidene]amino] 3-nitro-4,5-bis(phenylmethoxy)benzoate

HRID 62021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 62021
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([N+:26]([O-:28])=[O:27])[C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O/[N:30]=[C:31](\[NH2:42])/[C:32]1[CH:37]=[CH:36][CH:35]=[N:34][C:33]=1[C:38]([F:41])([F:40])[F:39]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([N+:26]([O-:28])=[O:27])[C:17]=1[O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:12]([O:14]/[N:30]=[C:31](\[NH2:42])/[C:32]1[CH:37]=[CH:36][CH:35]=[N:34][C:33]=1[C:38]([F:41])([F:39])[F:40])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 462019253,4-Bis(benzyloxy)-5-nitrobenzoic acidHCID 83401048HCID 83401048, Verbindung

Produkt 1

HCID 87544316[(Z)-[amino-[2-(trifluoromethyl)-3-pyridinyl]methylidene]amino] 3-nitro-4,5-bis(phenylmethoxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 3,4-bis(benzyloxy)-5-nitrobenzoic acid (0.759 g, 2 mmol) in dimethylformamide (10 mL) at room temperature was added 1,1-carbonyldiimidazole (0.34 g, 2.10 mmol) in one portion. The resulting yellow mixture was allowed to stir for ninety minutes whereupon (Z)—N′-hydroxy-2-(trifluoromethyl)nicotinimidamide (0.41 g, 2 mmol) was added in one portion. The resulting mixture was stifled at room temperature for two hours and then poured onto water (100 mL). The resulting precipitate was filtered off, washed with water and dried. After recrystallisation from dichloromethane/isopropanol, (Z)—N′-(3,4-bis(benzyloxy)-5-nitrobenzoyloxy)-2-(trifluoromethyl)nicotinimidamide was obtained as a light yellow solid, 0.88 g (78%).

Aufarbeitung

  1. additionwas added in one portion
  2. additionpoured onto water (100 mL)
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed with water
  5. customdried
  6. customAfter recrystallisation from dichloromethane/isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-bfc8d16801ea486c94860d5c14b24560
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09446012B2

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