Cyanogen Bromide → 5-[4-(Trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-amine

HRID 1023200

反応式

HRID 1023200 の反応式
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH:9][NH2:10])=[O:8])=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].[N:20]#[C:21]Br>O1CCOCC1.O>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:12]=[CH:11][C:6]([C:7]2[O:8][C:21]([NH2:20])=[N:10][N:9]=2)=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 5206624-(Trifluoromethyl)benzohydrazide

生成物 1

HCID 52160855-[4-(Trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-amine収率 50%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 4-(trifluoromethyl)benzohydrazide (0.5 g, 2.449 mmol) in dioxane (10 mL) and water (2 mL) was added sodium bicarbonate (0.617 g, 7.35 mmol) and cyanic bromide (0.519 g, 4.90 mmol). The reaction was stirred at room temperature for 15 h. The reaction mixture was diluted with water (50 mL), extracted with EtOAc, dried over sodium sulfate, and evaporated to yield 5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2-amine (0.28, 50%). 1H NMR: 400 MHz, DMSO-d6: δ 7.43 (s, 2H), 7.91 (d, J=8.40 Hz, 2H), 8.00 (d, J=8.40 Hz, 2H). LCMS: RT 1.55 min. LCMS (ES-API), m/z 230.0 (M+H).

後処理

  1. extractionextracted with EtOAc
  2. dry with materialdried over sodium sulfate
  3. customevaporated

出典と根拠

ORDレコード
ord-458df4e5b20243b1b4238d47b11dfe5c
出典データセット
uspto-grants-2014_05
特許番号
US08722670B2

関連ノート

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