Hydrazine, propyl- → 3-(4-Chlorophenyl)-7-[(4-chlorophenyl)methylene]-2,4,6,7-tetrahydro-1-propylthiopyrano[4,3-c]-pyrazole

HRID 1447799

反応式

HRID 1447799 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]2[C:14](=O)[C:13](=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:12][S:11][CH2:10]2)=[CH:4][CH:3]=1.[CH2:24]([NH:27][NH2:28])[CH2:25][CH3:26]>ClC(Cl)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:28][N:27]([CH2:24][CH2:25][CH3:26])[C:14]3[C:13](=[CH:16][C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=4)[CH2:12][S:11][CH2:10][C:9]2=3)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 42007Hydrazine, propyl-HCID 3824694H-Thiopyran-4-one, 3,5-bis[(4-chlorophenyl)methylene]tetrahydro-

生成物 1

HCID 544751963-(4-Chlorophenyl)-7-[(4-chlorophenyl)methylene]-2,4,6,7-tetrahydro-1-propylthiopyrano[4,3-c]-pyrazole収率 9%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

A mixture of tetrahydro-3,5-bis-(4-chlorophenylmethylene)-4H-thiopyran-4-one (6 g, 16.6 mmole) and N-propylhydrazine (1.3 g, 16.6 mmole) in dichloroethane (100 ml) is heated at reflux temperature for 2.5 hours and cooled to room temperature overnight. The reaction mixture is washed with dilute HCl and water, then dried over CaCl2. After the solvent is removed in vacuo, the residue (yellow solid) is chromatographed on a dry-packed Al2O3 column (neutral, activity I). The fractions eluted with 0-5% EtOAc/hexane give the major product. Further elution of the column with EtOAc, then with CHCl3, and after crystallization from acetoneacetonitrile, gives 0.6 g (9%) of the title compound in crystalline form (99% pure) m.p. 192°-194.5°.

後処理

  1. temperatureis heated
  2. temperatureat reflux temperature for 2.5 hours
  3. washThe reaction mixture is washed with dilute HCl and water
  4. dry with materialdried over CaCl2
  5. customAfter the solvent is removed in vacuo
  6. customthe residue (yellow solid) is chromatographed on a dry-packed Al2O3 column (neutral, activity I)
  7. washThe fractions eluted with 0-5% EtOAc/hexane
  8. customgive the major product
  9. washFurther elution of the column with EtOAc
  10. customwith CHCl3, and after crystallization from acetoneacetonitrile,

出典と根拠

ORDレコード
ord-f7f32b72cdb140a9b2f4d579f10f924a
出典データセット
uspto-grants-1979_12
特許番号
US04178379

関連ノート

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