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

HRID 1665619ノート

反応式

HRID 1665619 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fd8a93ad09ba4013be5ac8549662c757
出典データセット
uspto-grants-2011_10
特許番号
US08039463B2

反応ノート

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