Maleic Anhydride → 4-(Trifluoromethyl)benzohydrazide

HRID 523461

Reaktionsgleichung

Reaktionsgleichung von HRID 523461
C1[C@@H]2[C@H]3[C@@H]4C([N:12]([NH:15][C:16]([C:18]5[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=5)=[O:17])C(=O)[C@@H]4[C@@H]([C@H]12)C=C3)=O.O.C1CC=CC=CC=1.C1(=O)OC(=O)C=C1.NN.FC(F)(F)C1C=CC(C(OC)=O)=CC=1>C(O)(C)C.C1(C)C=CC=CC=1.CCCCCCC.C1(C)C=CC=CC=1>[F:25][C:24]([F:26])([F:27])[C:21]1[CH:22]=[CH:23][C:18]([C:16]([NH:15][NH2:12])=[O:17])=[CH:19][CH:20]=1

Komponenten

9

Edukt 5

HCID 7923Maleic AnhydrideHCID 9321HydrazineHCID 11000CycloheptatrieneHCID 520447Methyl 4-(trifluoromethyl)benzoateHCID 90479083Tecovirimat monohydrate

Produkt 1

HCID 5206624-(Trifluoromethyl)benzohydrazide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 3776IsopropanolLösungsmittelHCID 22263336Toluene heptaneLösungsmittel

Versuchsvorschrift

More specifically, to prepare ST-246 monohydrate, Form I, cycloheptatriene is reacted with maleic anhydride in the presence of toluene to yield the major product, endo isomer. The exo isomer is further produced from about 7% to 0.6% by crystallization from toluene/heptane. Further, hydrazine in the anhydrous or hydrate form is reacted with Methyl 4-(trifluoromethyl)benzoate in the presence of isopropanol to yield (4-(trifluoromethyl)-benzhydrazide. The product is then crystallized from isopropanol.

Aufarbeitung

  1. customto yield the major product, endo isomer

Quellen und Nachweise

ORD-Eintrag
ord-5de744a66bb9456fb5708ea16b86e461
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09339466B2

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