Triethylamine → 2-(5-Cyclopropyl-3-phenyl-isoxazol-4-yl)-5-(2-methoxy-phenyl)-[1,3,4]oxadiazole

HRID 2421158ノート

反応式

HRID 2421158 の反応式
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5]=2[C:15]([OH:17])=O)[CH2:3][CH2:2]1.[CH3:18][O:19][C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[C:22]([NH:24][NH2:25])=O.[Cl-].ClC1N(C)C=C[N+]=1C.C(N(CC)CC)C>ClCCl>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:5]=2[C:15]2[O:17][C:22]([C:21]3[CH:26]=[CH:27][CH:28]=[CH:29][C:20]=3[O:19][CH3:18])=[N:24][N:25]=2)[CH2:2][CH2:3]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 24051o-AnisohydrazideHCID 111266512-chloro-1,3-dimethyl-1H-imidazol-3-ium chlorideHCID 223090805-Cyclopropyl-3-phenyl-1,2-oxazole-4-carboxylic acid

生成物 1

HCID 167229072-(5-Cyclopropyl-3-phenyl-isoxazol-4-yl)-5-(2-methoxy-phenyl)-[1,3,4]oxadiazole収率 33%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of 5-cyclopropyl-3-phenyl-isoxazole-4-carboxylic acid (236 mg, 1.03 mmol) in dichloromethane (2 mL) were added 2-methoxybenzhydrazide (205 mg, 1.24 mmol), 2-chloro-1,3-dimethylimidazolium chloride (383 mg, 2.26 mmol) and triethylamine (0.52 ml, 5.15 mmol) at ambient temperature. The resulting suspension was stirred for 18 h at this temperature before diluting with dichloromethane (20 ml) and washing with water (20 mL) and brine (20 mL). The aqueous layers were extracted with dichlormethane and the combined organic layers dried over sodium sulfate. Purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=70:10:20 to 40:40:20) afforded the title compound (121 mg, 33%) as a white solid. MS: m/e=360.2 [M+H]+.

後処理

  1. washwashing with water (20 mL) and brine (20 mL)
  2. extractionThe aqueous layers were extracted with dichlormethane
  3. dry with materialthe combined organic layers dried over sodium sulfate
  4. customPurification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=70:10:20 to 40:40:20)

出典と根拠

ORDレコード
ord-8db7792f09f3414b8d81fc4ead911587
出典データセット
uspto-grants-2011_06
特許番号
US07956074B2

反応ノート

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