Thionyl Chloride → 3-Diethylamino-2,2-dimethylpropyl 5-(p-Chlorophenyl)-2-furoate Hydrochloride

HRID 892683

反応式

HRID 892683 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:20]([N:22]([CH2:29][CH3:30])[CH2:23][C:24]([CH3:28])([CH3:27])[CH2:25]O)[CH3:21]>C1C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([C:13]([O:15][CH2:25][C:24]([CH3:28])([CH3:27])[CH2:23][N:22]([CH2:29][CH3:30])[CH2:20][CH3:21])=[O:14])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 24386Thionyl Chloride2 回HCID 2959653-(Diethylamino)-2,2-dimethylpropan-1-olHCID 7266935-(4-Chlorophenyl)-2-furoic acid

生成物 1

HCID 197609533-Diethylamino-2,2-dimethylpropyl 5-(p-Chlorophenyl)-2-furoate Hydrochloride

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

実験手順

5-(p-Chlorophenyl)-2-furoic acid (33.5 g., 0.15 mole) is added with rapid stirring to thionyl chloride (58 ml.) at room temperature, heated until solution occurs (about 20 min.) and then refluxed for 2 hr. The mixture is stripped of excess thionyl chloride in vacuo, benzene (100 ml.) is added, and again stripped of solvent. The residue is treated with a solution of 3-diethylamino-2,2 dimethylpropanol (24.1 g., 0.15 mole) in benzene (700 ml.), refluxed for 4 hr., cooled, diluted with petroleum ether (450 ml.) and stored for 18 hours at room temperature. The benzene-petroleum ether solution is decanted, the residue is dissolved in H2O (1000 ml.), and the solution is adjusted to pH 8 with saturated aqueous Na2CO3 (70 ml.). The product is extracted from the aqueous phase with benzene (1000 ml.) in portions and the extract is dried overnight with MgSO4 and activated charcoal. The solution is filtered and the filtrate is adjusted to pH 3 with ether-HCl (cooled in ice bath). Petroleum ether (300 ml.) is added and the product oiled out of solution. The benzene-petroleum ether solution is decanted and the product is washed twice with anhydrous ether (scratching induced crystallization). The solid is recrystallized from ethanol (200 ml.) to yield: 32 g. (53%). A sample is recrystallized twice from isopropanol, m.p. 139°-143°.

後処理

  1. temperatureheated until solution
  2. custom(about 20 min.)
  3. temperaturerefluxed for 2 hr
  4. additionis added
  5. temperaturerefluxed for 4 hr
  6. temperature, cooled
  7. customThe benzene-petroleum ether solution is decanted
  8. dissolutionthe residue is dissolved in H2O (1000 ml.)
  9. extractionThe product is extracted from the aqueous phase with benzene (1000 ml.) in portions
  10. dry with materialthe extract is dried overnight with MgSO4 and activated charcoal
  11. filtrationThe solution is filtered
  12. additionPetroleum ether (300 ml.) is added
  13. customThe benzene-petroleum ether solution is decanted
  14. washthe product is washed twice with anhydrous ether (scratching induced crystallization)
  15. customThe solid is recrystallized from ethanol (200 ml.) to yield: 32 g
  16. customA sample is recrystallized twice from isopropanol, m.p. 139°-143°

出典と根拠

ORDレコード
ord-f3e4f2ea857f4c00992fce448eaff0e3
出典データセット
uspto-grants-1992_06
特許番号
US05118708

関連ノート

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