Dimethylformamide → 5-Chloro-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole

HRID 405824ノート

反応式

HRID 405824 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11](=O)[O:10][N:9]=2)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].CN(C)C=O.O=P(Cl)(Cl)[Cl:24]>>[Cl:24][C:11]1[O:10][N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:14]([O-:16])=[O:15])[CH:4]=2)[N:12]=1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 1363340393-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazol-5(4H)-one

生成物 1

HCID 712813525-Chloro-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole

実験手順

To a solution of 3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazol-5(4H)-one (106) (12 g, 54.26 mmol) in POCl3 (120 mL) was added N,N-dimethylformamide (12 mL). The resulted solution was heated to reflux for 72 hours then concentrated under vacuum. The residue was dissolved in water (250 mL) and extracted with ethyl acetate (3×250 mL). The combined organic layers were washed with brine (3×250 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by flash chromatography (PE/EA=10:1) to afford 5-chloro-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole (107) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.64 (dd, J=1.5, 8.4 Hz, 1H), 8.18 (dd, J=1.5, 7.8 Hz, 1H), 7.56 (d, J=8.1 Hz, 1H), 2.70 (s, 3H). MS m/z 240.7 (M+1)+.

後処理

  1. temperatureThe resulted solution was heated
  2. temperatureto reflux for 72 hours
  3. concentrationthen concentrated under vacuum
  4. dissolutionThe residue was dissolved in water (250 mL)
  5. extractionextracted with ethyl acetate (3×250 mL)
  6. washThe combined organic layers were washed with brine (3×250 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by flash chromatography (PE/EA=10:1)

出典と根拠

ORDレコード
ord-f8d7b1ae27e741c186e90fa2e9bcd2b8
出典データセット
uspto-grants-2014_06
特許番号
US08754071B2

反応ノート

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