Furfural → HCID 178420175、化合物

HRID 589291ノート

反応式

HRID 589291 の反応式
[CH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[O:3][CH:2]=1.O[N:9]=[C:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1CCCCC1.C1(C)C=CC=CC=1>[O:3]1[CH:2]=[CH:1][CH:5]=[C:4]1[CH:6]1[O:7][N:9]=[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:17]1

参加物

5

反応物 2

HCID 7362FurfuralHCID 69186N'-Hydroxybenzenecarboximidamide

生成物 1

HCID 178420175HCID 178420175、化合物収率 43.2%

試薬・触媒・溶媒 2

HCID 8082Piperidine触媒HCID 1140Toluene溶媒

実験手順

A mixture of 2-furfural (1.0 mL, 1.17 g, 12.2 mmol, 1.5 equivalents), N′-hydroxybenzimidamide (1.11 g, 8.1 mmol) and one drop of piperidine in toluene (100 mL) was heated to reflux for 18 hours in a SOXHLETT apparatus that was charged with SILCARBON 3 Angstrom molecular sieve (8 g). The reaction mixture was allowed to cool to room temperature, and the solvent was removed in vacuo. After purification by automated column chromatography on an ISCO COMPANION apparatus (SiO2, gradient heptane/ethyl acetate), the 5-(furan-2-yl)-3-phenyl-4,5-dihydro-1,2,4-oxadiazole product (745 mg, 3.5 mmol) was obtained as a brown oil that solidified to a tan solid upon standing. The overall reaction yield was approximately 43%. LC-MS [M+H] 215 (C12H10N2O2+H, expected 215.07].

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours in a SOXHLETT apparatus that
  3. additionwas charged with SILCARBON 3 Angstrom molecular sieve (8 g)
  4. customthe solvent was removed in vacuo
  5. customAfter purification by automated column chromatography on an ISCO COMPANION apparatus (SiO2, gradient heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-13b71fcdc0e74ce5a651b1bb185fc890
出典データセット
uspto-grants-2016_01
特許番号
US09232800B2

反応ノート

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