Oxalyl chloride → Ethyl 5-(4-methylbenzyl)-1,2,4-oxadiazole-3-carboxylate

HRID 58610

반응식

HRID 58610 반응식
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=O)=[CH:3][CH:2]=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>[CH3:11][C:1]1[CH:2]=[CH:3][C:4]([CH2:7][C:8]2[O:10][N:25]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:18]=2)=[CH:5][CH:6]=1

참가 물질

8

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 248474p-Tolylacetic acidHCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetate

생성물 1

HCID 63382896Ethyl 5-(4-methylbenzyl)-1,2,4-oxadiazole-3-carboxylate수율 23%

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

This compound was prepared according to general method 2 with (step I) 2-p-tolylacetic acid (0.568 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 (12 mL). The crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.2118 g (23%) of ethyl 5-(4-methylbenzyl)-1,2,4-oxadiazole-3-carboxylate as a yellow solid.

후처리

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

출처 및 근거

ORD 기록
ord-efa837457daa4f81904735729d124585
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434722B2

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