Ethyl orthoformate → HCID 135744212、化合物

反応式

[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.[CH2:13](OC(OCC)OCC)C>>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[O:7][CH:13]=[N:9][N:8]=2)=[C:4]([OH:12])[CH:3]=1

参加物

反応物 2

HCID 31214Ethyl orthoformate

HCID 49964814-chloro-2-hydroxybenzohydrazide

生成物 1

HCID 135744212HCID 135744212、化合物収率 35%

反応条件

温度: 130 °C

実験手順

A mixture of 4-chloro-2-hydroxybenzoic acid hydrazide (Chemical Abstracts, 93:7808, 475 mg, 2.55 mmol) and triethylorthoformate. (3.6 ml) is heated at 130° C. for 3.5 hours. After cooling, a precipitate formed and is collected by filtration. The filter cake is recrystallized from methanol to give 173 mg (35%) of 5-chloro-2-(1,3,4-oxadiazol-2-yl)phenol. This phenolic product is reacted with (2S)-glycidyl 3-nitrobenzenesulfonate substantially as described for Epoxide 1 to yield 170 mg (69%) of the title epoxide.

後処理

temperatureAfter cooling
customa precipitate formed
filtrationis collected by filtration
customThe filter cake is recrystallized from methanol

出典と根拠

ORDレコード: ord-d88f3995ee7a4feb9258937e4e340117
出典データセット: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US06730792B2

反応ノート

読み込み中…

参加物