3-(Trifluoromethyl)aniline → N'-hydroxy-4-[(2-methoxyethyl)amino]-N-[3-(trifluoromethyl)phenyl]-1,2,5-oxadiazole-3-carboximidamide

HRID 69787

反応式

HRID 69787 の反応式
[OH:1][N:2]=[C:3](Cl)[C:4]1[C:8]([NH:9][CH2:10][CH2:11][O:12][CH3:13])=[N:7][O:6][N:5]=1.[F:15][C:16]([F:25])([F:24])[C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O.[Cl-].[Na+].O>[OH:1][N:2]=[C:3]([C:4]1[C:8]([NH:9][CH2:10][CH2:11][O:12][CH3:13])=[N:7][O:6][N:5]=1)[NH:20][C:19]1[CH:21]=[CH:22][CH:23]=[C:17]([C:16]([F:15])([F:24])[F:25])[CH:18]=1

参加物

7

反応物 4

HCID 73753-(Trifluoromethyl)anilineHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 136330165N-Hydroxy-4-[(2-methoxyethyl)amino]-1,2,5-oxadiazole-3-carboximidoyl chloride

生成物 1

HCID 178495896N'-hydroxy-4-[(2-methoxyethyl)amino]-N-[3-(trifluoromethyl)phenyl]-1,2,5-oxadiazole-3-carboximidamide収率 81.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 57417360Sodium chloride; water溶媒

反応条件

温度
60 °C

実験手順

N-Hydroxy-4-[(2-methoxyethyl)amino]-1,2,5-oxadiazole-3-carboximidoyl chloride (1.3 g, 5.0 mmol) [made according to Example 1, steps A through E] was stirred in water (10 mL) and warmed to 60° C. for 5 minutes. 3-(trifluoromethyl)aniline [Aldrich, product # A41801] (880 mg, 5.5 mmol) was added in one portion and the reaction stirred for 15 minutes. While remaining at 60° C., a solution of sodium bicarbonate (630 mg, 7.5 mmol) in water (10 mL) was added dropwise over 5 minutes. The reaction was stirred at 60° C. for an additional 50 minutes, and then allowed to cool to room temperature. Ethyl acetate (20 mL) and brine (30 mL) were added to the flask and the organic layer was collected. The aqueous layer was extracted with ethyl acetate (2×20 mL) and the combined organics were dried over sodium sulfate. The solvent was removed in vacuo to give the desired product as an orange solid (1.4 g, 80%). LCMS calculated for C13H15F3N5O3 (M+H)+: m/z=346.1. 1H NMR (400 MHz, CD3OD): δ 7.36 (t, J=8.2 Hz, 1H), 7.23 (d, J=7.6 Hz, 1H), 7.09 (s, 1H), 7.02 (d, J=8.2 Hz, 1H), 3.60 (t, J=5.2 Hz, 2H), 3.46 (t, J=5.2 Hz, 2H), 3.38 (s, 3H).

後処理

  1. customWhile remaining at 60° C.
  2. stirringThe reaction was stirred at 60° C. for an additional 50 minutes
  3. temperatureto cool to room temperature
  4. customthe organic layer was collected
  5. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
  6. dry with materialthe combined organics were dried over sodium sulfate
  7. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-24817404dfce438d865660eacfa23cfb
出典データセット
uspto-grants-2014_09
特許番号
US08822511B2

関連ノート

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