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

HRID 1447799

반응식

HRID 1447799 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

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°.

후처리

  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,

출처 및 근거

ORD 기록
ord-f7f32b72cdb140a9b2f4d579f10f924a
출처 데이터셋
uspto-grants-1979_12
특허 번호
US04178379

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