Hydroxylamine → 3-[3-(tetrahydro-pyran-2-yloxymethyl)-phenyl]-4H-[1,2,4]oxadiazol-5-one

HRID 1161111ノート

反応式

HRID 1161111 の反応式
N[OH:2].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15].[C:19]([N:26]1C=CN=C1)(N1C=CN=C1)=[O:20].O>C(O)(C)C.O1CCOCC1>[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH2:10][C:11]1[CH:12]=[C:13]([C:14]2[NH:26][C:19](=[O:20])[O:2][N:15]=2)[CH:16]=[CH:17][CH:18]=1

参加物

7

反応物 4

HCID 787HydroxylamineHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 219279093-(Tetrahydro-pyran-2-yloxymethyl)-benzonitrile

生成物 1

HCID 1363488113-[3-(tetrahydro-pyran-2-yloxymethyl)-phenyl]-4H-[1,2,4]oxadiazol-5-one収率 89.5%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 312751,4-Dioxane溶媒

実験手順

Add 50% aqueous hydroxylamine (9.73 g, 147 mmol) dropwise to a refluxing solution of 3-(tetrahydro-pyran-2-yloxymethyl)-benzonitrile (8.00 g, 36.8 mmol) in isopropanol (0.1M). After 2 hours, cool to room temperature and concentrate under reduced pressure to give a residue. Dissolve the residue in dioxane (0.1M). Add carbonyldiimidazole (7.16 g, 44.2 mmol) and heat to 110° C. After 30 minutes, cool to room temperature and pour into water. Extract with ethyl acetate. Combine the organic layers, dry with sodium sulfate, filter and concentrate under reduced pressure to yield the title product as a white solid (9.10 g, 89%): 1H NMR (CDCl3) δ 1.53-1.95 (m, 6H), 3.59 (m, 1H), 3.93 (m, 1H), 4.58 (d, 1H), 4.77 (t, 1H), 4.88 (d, 1H), 7.52 (t, 1H), 7.57 (d, 1H), 7.71 (d, 1H), 7.82 (s, 1H), 11.16 (bs, 1H)

後処理

  1. concentrationconcentrate under reduced pressure
  2. customto give a residue
  3. waitAfter 30 minutes
  4. temperaturecool to room temperature
  5. extractionExtract with ethyl acetate
  6. dry with materialdry with sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure

出典と根拠

ORDレコード
ord-55606058096a4cd58151145fd10f67fb
出典データセット
uspto-grants-2010_10
特許番号
US07816523B2

反応ノート

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