Hydrochloric Acid → 4,4'-Diacetamidostilbene

HRID 2379248

反応式

HRID 2379248 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.Cl.[C:18](OC(=O)C)(=[O:20])[CH3:19].[C:25]([O-])(=[O:27])[CH3:26].[Na+]>O>[C:18]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:25](=[O:27])[CH3:26])=[CH:14][CH:15]=2)=[CH:6][CH:7]=1)(=[O:20])[CH3:19]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 92134{4-[(E)-2-(4-aminophenyl)vinyl]phenyl}amineHCID 517045Sodium Acetate

生成物 1

HCID 27505224,4'-Diacetamidostilbene

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

4,4'-Diaminostilbene (8.9 grams, 0.0847 --NH2 equivalent) from B above, is ground to a fine powder and added to a beaker containing stirred, 90° C. deionized water (1500 milliliters). After two minutes, aqueous 36.5% hydrochloric acid (8.47 grams, 0.0847 mole) is added to the stirred, 90° C. suspension. The solution which formed within five minutes is cooled to 60° C. Acetic anhydride (10.61 grams, 0.1039 mole) is added to the stirred solution and mixed therein for 30 seconds before addition of an aqueous sodium acetate solution (prepared by dissolution of anhydrous sodium acetate [13.89 grams, 0.1693 mole] in deionized water [41.7 grams]). After thoroughly stirring the white slurry, it is maintained at 4° C. for 16 hours, followed by filtration to remove the precipitated product. The recovered filter cake is washed with two portions (250 milliliters) of deionized water then dried in a vacuum oven at 80° C. and 2 mm Hg to a constant weight of 11.44 grams. The product is recovered as a tan colored crystalline powder. Fourier transform infrared spectrophotometric analysis of a potassium chloride pellet of the product confirms the product structure: disappearance of the absorbances observed for the --NH2 group, appearance of solid state >NH stretching absorbances at 3309 (3396 and 3190 shoulders) cm-1, a solid state amide I carbonyl stretching absorbance at 1669 cm-1, a solid state amide II carbonyl stretching absorbance at 1516 cm-1 (masking the aromatic ring absorbance), an out-of-plane C--H deformation at 959 cm-1 due to the trans substituted ethylene group and a C--H out-of-plane bending vibration at 832 cm-1 due to the para-disubstituted aromatic rings. Proton nuclear magnetic resonance spectroscopy further confirms the product structure.

後処理

  1. additionadded to a beaker
  2. additioncontaining
  3. customThe solution which formed within five minutes
  4. temperatureis cooled to 60° C
  5. additionmixed
  6. stirringAfter thoroughly stirring the white slurry, it
  7. temperatureis maintained at 4° C. for 16 hours
  8. filtrationfollowed by filtration
  9. customto remove the precipitated product
  10. filtrationThe recovered filter cake
  11. washis washed with two portions (250 milliliters) of deionized water
  12. customthen dried in a vacuum oven at 80° C.
  13. customThe product is recovered as a tan colored crystalline powder

出典と根拠

ORDレコード
ord-66443b7f42bd4277919982649ed350b9
出典データセット
uspto-grants-1994_11
特許番号
US05360884

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