N-Hydroxyacetamidine → 5-{[4-(Methanesulfonyl)phenyl]methyl}-3-methyl-1,2,4-oxadiazole

HRID 2187902ノート

反応式

HRID 2187902 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:27](=[N:30]O)([NH2:29])[CH3:28]>CN(C=O)C>[CH3:28][C:27]1[N:30]=[C:12]([CH2:11][C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=2)[O:14][N:29]=1

参加物

5

反応物 3

HCID 30926N-HydroxyacetamidineHCID 682631,1'-CarbonyldiimidazoleHCID 5723454-Mesylphenylacetic acid

生成物 1

HCID 99212855-{[4-(Methanesulfonyl)phenyl]methyl}-3-methyl-1,2,4-oxadiazole

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-(methylsulfonyl)phenylacetic acid (15 g, 70 mmol) in DMF (300 mL) at r.t., was added carbonyldiimidazole (12.5 g, 77 mmol). After 0.5 h at r.t., acetamide oxime (5.7 g, 77 mmol) was added. After stirring the resulting mixture overnight at r.t., the mixture was heated to 120° C. for 6 h. After cooling to r.t., the mixture was quenched with H2O, and extracted with EtOAc. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (Hex:EtOAc, 1:1) yielded (3-Methyl-1,2,4-oxadiazol-5-yl) [4-(methylsulfonyl)phenyl]methane.

後処理

  1. temperaturethe mixture was heated to 120° C. for 6 h
  2. temperatureAfter cooling to r.t.
  3. customthe mixture was quenched with H2O
  4. extractionextracted with EtOAc
  5. washThe organic extracts were washed (H2O, brine)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash chromatography (Hex:EtOAc, 1:1)

出典と根拠

ORDレコード
ord-55247a372dda474da846723c76d62d55
出典データセット
uspto-grants-2002_06
特許番号
US06410563B1

反応ノート

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