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

HRID 1161111노트

반응식

HRID 1161111 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 312751,4-Dioxane용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-55606058096a4cd58151145fd10f67fb
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816523B2

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