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

HRID 892682

反応式

HRID 892682 の反応式
[F: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:18])=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:18].[F: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 7389915-(4-Fluorophenyl)furan-2-carboxylic acid

生成物 1

HCID 197608813-Diethylamino-2,2-dimethylpropyl 5-(p-Fluorophenyl)-2-furoate Hydrochloride

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

実験手順

5-(p-Fluorophenyl)-2-furoic acid (18.6 g., 0.09 mole) is added with rapid stirring to thionyl chloride (31.5 ml.) at room temperature, heated until solution occurs (about 1/4 hr.) and then is 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 reside is treated with a solution of 3-diethylamino-2,2-dimethylpropanol (14.5 g. 0.09 mole) in benzene (490 ml.) is refluxed for 3 hr., cooled, is diluted with petroleum ether (300 ml.), and is stored for 2 days at room temperature. The benzene-petroleum ether solution is decanted, the residue dissolved in H2O (750 ml.) and the solution adjusted to pH 8 with saturated aqueous Na2CO3 (75 ml.). The product is extracted from the aqueous phase with benzene (860 ml.) in portions and the extract dried for hours over MgSO4 and activated charcoal. The solution is filtered and the filtrate adjusted to pH 3 with ether-HCl (cooled in ice bath). Petroleum ether (400 ml.) is added and the product oiled out of solution. The benzene-petroleum ether solution is decanted and the product washed twice with anhydrous ether (scratching induced crystallization). The solid is recrystallized from isopropanol (200 ml.) to yield 16.9 g. (49%). A sample is recrystallized from isopropanol, m.p. 134°-138°.

後処理

  1. temperatureheated until solution
  2. custom(about 1/4 hr.)
  3. temperatureis refluxed for 2 hr
  4. additionis added
  5. temperatureis refluxed for 3 hr
  6. temperature, cooled
  7. customThe benzene-petroleum ether solution is decanted
  8. dissolutionthe residue dissolved in H2O (750 ml.)
  9. extractionThe product is extracted from the aqueous phase with benzene (860 ml.) in portions
  10. dry with materialthe extract dried for hours over MgSO4 and activated charcoal
  11. filtrationThe solution is filtered
  12. additionPetroleum ether (400 ml.) is added
  13. customThe benzene-petroleum ether solution is decanted
  14. washthe product washed twice with anhydrous ether (scratching induced crystallization)
  15. customThe solid is recrystallized from isopropanol (200 ml.)
  16. customto yield 16.9 g
  17. customA sample is recrystallized from isopropanol, m.p. 134°-138°

出典と根拠

ORDレコード
ord-419153d1b6a44587810d496230357f40
出典データセット
uspto-grants-1992_06
特許番号
US05118708

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