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

HRID 1023200

반응식

HRID 1023200 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-458df4e5b20243b1b4238d47b11dfe5c
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722670B2

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