Malononitrile → [3-(4-Chlorobenzoyl)-1,2,4-oxadiazol-5-yl]acetonitrile

HRID 638562노트

반응식

HRID 638562 반응식
[CH:1]1[C:6]([C:7](/[C:9](/Cl)=[N:10]/[OH:11])=[O:8])=[CH:5][CH:4]=[C:3]([Cl:13])[CH:2]=1.[C:14](#[N:18])[CH2:15][C:16]#[N:17]>C1(C)C=CC=CC=1>[Cl:13][C:3]1[CH:4]=[CH:5][C:6]([C:7]([C:9]2[N:17]=[C:16]([CH2:15][C:14]#[N:18])[O:11][N:10]=2)=[O:8])=[CH:1][CH:2]=1

참가 물질

4

반응물 2

HCID 8010MalononitrileHCID 9614280(1Z)-2-(4-chlorophenyl)-N-hydroxy-2-oxoethanimidoyl chloride

생성물 1

HCID 13576490[3-(4-Chlorobenzoyl)-1,2,4-oxadiazol-5-yl]acetonitrile수율 28%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 38 g of 4-chlorophenylglyoxylohydroxamyl chloride and 112 g of malononitrile in one liter of toluene was refluxed for 48 hours under N2. The cooled mixture was filtered and concentrated in vacuo. The residue was taken up in Et2O, washed with water (8×) and brine, and dried over MgSO4. Concentration gave an oil which was purified by high pressure liquid chromatography using 5% hexane/CH2Cl2 as an eluent to give 12 g (28%) of an oil which solidified on standing, m.p. 81°-84°.

후처리

  1. temperaturewas refluxed for 48 hours under N2
  2. filtrationThe cooled mixture was filtered
  3. concentrationconcentrated in vacuo
  4. washwashed with water (8×) and brine
  5. dry with materialdried over MgSO4
  6. concentrationConcentration
  7. customgave an oil which
  8. customwas purified by high pressure liquid chromatography

출처 및 근거

ORD 기록
ord-2271abff3fb14d348a65858cae8cb0cf
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04562186

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