Acetic Acid → 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenylmethanamine

HRID 1772419

반응식

HRID 1772419 반응식
[F:1][C:2]([F:34])([F:33])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:32]=[CH:31][C:18]([CH2:19][NH:20]C(=O)OCC4C=CC=CC=4)=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.C(O)(=O)C.C(OCC)C>Br>[F:34][C:2]([F:1])([F:33])[O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:32]=[CH:31][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=3)=[N:11]2)=[CH:8][CH:9]=1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 90404490benzyl 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylcarbamate

생성물 1

HCID 904040894-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenylmethanamine수율 74%

시약·촉매·용매 1

HCID 260Hydrogen Bromide용매

실험 절차

In a 200 mL round bottomed flask equipped with a magnetic stir bar, benzyl 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylcarbamate (C14) (0.850 g, 1.82 mmol) was diluted with a solution of hydrogen bromide in acetic acid (33 wt %, 15.0 mL, 1.82 mmol). The suspension was allowed to stir for 1 hour. Diethyl ether (150 mL) was added, and the reaction mixture was stirred for an additional 30 minutes. The resulting precipitate was collected via filtration and treated with aqueous sodium hydroxide. The resulting suspension was extracted with ethyl acetate (3×75 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated to afford the title compound as a white solid (0.448 g, 74%): 1H NMR (400 MHz, DMSO-d6) δ 9.39 (s, 1H), 8.07 (dd, J=10.6, 8.6 Hz, 4H), 7.69-7.56 (m, 2H), 7.48 (d, J=8.2 Hz, 2H), 3.79 (s, 2H); 19F NMR (376 MHz, DMSO-d6) δ −56.98; ESMIS m/z 318 ([M+H]+) (—NH2).

후처리

  1. customIn a 200 mL round bottomed flask equipped with a magnetic stir bar
  2. stirringthe reaction mixture was stirred for an additional 30 minutes
  3. filtrationThe resulting precipitate was collected via filtration
  4. additiontreated with aqueous sodium hydroxide
  5. extractionThe resulting suspension was extracted with ethyl acetate (3×75 mL)
  6. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0aa9ae96f157419a9ed36de16a57c77a
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249133B2

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