O-Xylene → 3-(1,3,4-Thiadiazol-2-yl)pyridine

HRID 329608

反応式

HRID 329608 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2O[CH:9]=[N:10][N:11]=2)[CH:2]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:13].C1(C)C(C)=CC=CC=1>O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:13][CH:9]=[N:10][N:11]=2)[CH:2]=1

参加物

5

反応物 3

HCID 7237O-XyleneHCID 14817Phosphorus sulfide (P2S5)HCID 40231652-(Pyridin-3-yl)-1,3,4-oxadiazole

生成物 1

HCID 198712843-(1,3,4-Thiadiazol-2-yl)pyridine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 5.5 g of the above prepared 2-(3-pyridyl)-1,3,4-oxadiazole, 8.5 g of phosphorus pentasulfide and 70 ml of xylene is stirred for 16 hours at 150°-160° C. To the cooled reaction mixture are added 50 ml of water and stirring is continued for another 5 minutes. The reaction mixture is then filtered. The filter residue is taken up in 100 ml of 10% sodium hydroxide solution. After extraction with chloroform, the organic phase is washed with water, dried and concentrated. After purification by column chromatography over silica gel with a 95:5 mixture of chloroform/ethanol as eluant, the crude 2-(3-pyridyl)-1,3,4-thiadiazole (compound 1) of the formula ##STR8## with a melting point of 64°-67° C., is obtained.

後処理

  1. additionA mixture of 5.5 g of the
  2. customTo the cooled reaction mixture
  3. stirringstirring
  4. waitis continued for another 5 minutes
  5. filtrationThe reaction mixture is then filtered
  6. extractionAfter extraction with chloroform
  7. washthe organic phase is washed with water
  8. customdried
  9. concentrationconcentrated
  10. customAfter purification by column chromatography over silica gel
  11. additionwith a 95:5 mixture of chloroform/ethanol as eluant

出典と根拠

ORDレコード
ord-a2c580c2c4c74133a7367a1650251ce9
出典データセット
uspto-grants-1990_01
特許番号
US04892880

関連ノート

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