Hydrochloric Acid → 2-Chloro-3-(trifluoromethyl)benzohydrazide

HRID 576707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 576707
[Cl:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(C1NC=CN=1)(C1NC=CN=1)=O.O.[NH2:28][NH2:29].Cl>C1COCC1>[Cl:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:28][NH2:29])=[O:5]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 27366772-Chloro-3-(trifluoromethyl)benzoic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone2×

Produkt 1

HCID 665991052-Chloro-3-(trifluoromethyl)benzohydrazideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 2-chloro-3-(trifluoromethyl)benzoic acid (1.0 g, 4.5 mmol) in THF (7 mL) was added carbonyl diimidazole (939 mg, 5.8 mmol). After 40 minutes, additional carbonyl diimidazole (200 mg, 1.2 mmol) was added and stirring was continued for 30 minutes. This solution was added dropwise to a separate flask containing hydrazine monohydrate (0.44 mL, 8.9 mmol) in THF (8 mL). After 1 h, 1M HCl was added, and the reaction mixture was extracted with 20% IPA/CHCl3 (×3). The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated to afford the desired product as a white solid (1.0 g, 94%). MS (ESI): mass calcd. for C8H6ClF3N2O, 238.0; m/z found, 239.0 [M+H]+. 1H NMR (500 MHz, MeOD) δ 7.87 (dd, J=7.9, 1.3 Hz, 1H), 7.72-7.63 (m, 1H), 7.56 (t, J=7.8 Hz, 1H), 7.05 (s, 1H).

Aufarbeitung

  1. waitwas continued for 30 minutes
  2. additionThis solution was added dropwise to a separate flask
  3. waitAfter 1 h
  4. extractionthe reaction mixture was extracted with 20% IPA/CHCl3 (×3)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a0d7372aa6e2479fbe14267a706ec71f
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040534B2

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