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

HRID 576707노트

반응식

HRID 576707 반응식
[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]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 27366772-Chloro-3-(trifluoromethyl)benzoic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone2회

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a0d7372aa6e2479fbe14267a706ec71f
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040534B2

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