Ammonium Chloride → 4-(1,2,4-Oxadiazol-3-yl)aniline

HRID 1665619노트

반응식

HRID 1665619 반응식
[Cl-].[NH4+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]=[CH:15][O:14][N:13]=2)=[CH:8][CH:7]=1)([O-])=O>O.C1COCC1.[Zn]>[O:14]1[CH:15]=[N:16][C:12]([C:9]2[CH:10]=[CH:11][C:6]([NH2:3])=[CH:7][CH:8]=2)=[N:13]1

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 27982883-(4-Nitrophenyl)-1,2,4-oxadiazole

생성물 1

HCID 214837044-(1,2,4-Oxadiazol-3-yl)aniline수율 96.2%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Ammonium chloride (214 mg, 4 mmol) in water (5 mL) was added to a stirred solution of 3-(4-nitro-phenyl)-[1,2,4]oxadiazole (200 mg, 1 mmol) in THF (15 mL). Zinc powder (262 mg, 4 mmol) was then added portion wise. The reaction was stirred at room temperature for 1 hour and then refluxed at 65° C. for 5 hours. The mixture was filtered over celite, the filtrate was evaporated and the residue was extracted with ethyl acetate. The ethyl acetate was washed with brine solution, dried over Na2SO4 and evaporated to afford 155 mg (92%) of 4-[1,2,4]oxadiazol-3-yl-phenylamine. 1H NMR: (DMSO-d6): δ 9.5 (s, 1H), 7.7 (d, 2H), 6.7 (d, 2H), 5.8 (s, 2H).

후처리

  1. temperaturerefluxed at 65° C. for 5 hours
  2. filtrationThe mixture was filtered over celite
  3. customthe filtrate was evaporated
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe ethyl acetate was washed with brine solution
  6. dry with materialdried over Na2SO4
  7. customevaporated

출처 및 근거

ORD 기록
ord-fd8a93ad09ba4013be5ac8549662c757
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039463B2

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