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

HRID 573818

反応式

HRID 573818 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 260Hydrogen Bromide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ea1c86663ab44162bf742df178e7eeef
出典データセット
uspto-grants-2015_05
特許番号
US09029560B2

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