3-Chlorophenylacetic acid → Ethyl 5-(3-chlorobenzyl)-1,2,4-oxadiazole-3-carboxylate

HRID 58601

反応式

HRID 58601 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.[NH2:18][C:19](=[N:25]O)[C:20]([O:22][CH2:23][CH3:24])=[O:21].C(N(CC)C(C)C)(C)C>ClCCl.N1C=CC=CC=1.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][C:9]1[O:11][N:25]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:18]=1

参加物

8

反応物 4

HCID 158793-Chlorophenylacetic acidHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetate

生成物 1

HCID 63379544Ethyl 5-(3-chlorobenzyl)-1,2,4-oxadiazole-3-carboxylate収率 28.1%

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

This compound was prepared according to general method 2 with (step I) 2-(3-chlorophenyl)acetic acid (0.646 g; 3.78 mmol) and oxalyl chloride (0.352 mL; 4.16 mmol) in dichloromethane (12 mL) with few drops of DMF and (step II) ethyl 2-amino-2-(hydroxyimino)acetate (0.5 g; 3.78 mmol) and N,N diisopropylethylamine (1.05 mL; 6.06 mmol) in dichloromethane (6 mL) and (step III) pyridine (18 mL). The crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.283 g (28%) of ethyl 5-(3-chlorobenzyl)-1,2,4-oxadiazole-3-carboxylate as a white solid.

後処理

  1. customThis compound was prepared
  2. customThe crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-605d83d794bc47fc93088dfaa8adf4b2
出典データセット
uspto-grants-2016_09
特許番号
US09434722B2

関連ノート

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