N,N-Dimethylbenzylamine → N-(p-sulfophenyl)-cinnamamide

HRID 1263050

반응식

HRID 1263050 반응식
[S:1]([OH:11])(=[O:10])([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)=[O:2].CN(CC1C=CC=CC=1)C.[C:22](Cl)(=[O:31])[CH:23]=[CH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC(C)=O>[S:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:22](=[O:31])[CH:23]=[CH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:7][CH:8]=1)([OH:11])(=[O:10])=[O:2]

참가 물질

5

반응물 3

HCID 7681N,N-DimethylbenzylamineHCID 8479Sulfanilic acidHCID 660233-Phenylprop-2-enoyl chloride

생성물 1

HCID 3021415N-(p-sulfophenyl)-cinnamamide수율 75.9%

시약·촉매·용매 1

HCID 180Acetone용매2회

반응 조건

온도
30 °C

실험 절차

To a suspension of 86.5 g of anhydrous sulphanilic acid in 120 g of acetone are added dropwise, while stirring at 30° C., 168.8 g of N,N-dimethyl-benzylamine in the course of 15 minutes, followed by a solution of 83.5 g of cinnamoyl chloride in 80 g of acetone in the course of 50 minutes. After the addition is complete, the reaction temperature is increased to the reflux temperature for 1 hour, and the acetone is then removed as completely as possible. The residue which remains is stirred for 1 hour at 80° C., 90 g of 50% strength sodium hydroxide solution in 500 ml of water are then added, and the mixture is again heated to 80° C. and left to stand at this temperature for 15 minutes. The phases are separated and the aqueous phase is washed with 50 g of toluene. The aqueous phase, which is still hot, is diluted with 800 ml of water and neutralized with concentrated sulphuric acid. The cooled aqueous solution is then added dropwise in the course of 20 minutes to 1 kg of 50% strength sulphuric acid, while stirring vigorously. The precipitated crystals are separated off and dissolved in 4 liters of water, the solution is filtered, and again brought to crystallization by the addition of 100 g of concentrated sulphuric acid. 111 g of pure N-(p-sulfophenyl)-cinnamamide (corresponding to 75.9% of theory) with a melting point of 235°-237° C. are obtained. UV spectrum (in methanol):

후처리

  1. additionare added dropwise
  2. customin the course of 15 minutes
  3. additionAfter the addition
  4. temperaturethe reaction temperature is increased to the reflux temperature for 1 hour
  5. customthe acetone is then removed as completely as possible
  6. stirringThe residue which remains is stirred for 1 hour at 80° C.
  7. addition90 g of 50% strength sodium hydroxide solution in 500 ml of water are then added
  8. temperaturethe mixture is again heated to 80° C.
  9. waitleft
  10. customThe phases are separated
  11. washthe aqueous phase is washed with 50 g of toluene
  12. additionis diluted with 800 ml of water and neutralized with concentrated sulphuric acid
  13. additionThe cooled aqueous solution is then added dropwise in the course of 20 minutes to 1 kg of 50% strength sulphuric acid
  14. stirringwhile stirring vigorously
  15. customThe precipitated crystals are separated off
  16. dissolutiondissolved in 4 liters of water
  17. filtrationthe solution is filtered
  18. customagain brought to crystallization by the addition of 100 g of concentrated sulphuric acid

출처 및 근거

ORD 기록
ord-75e32475d7964271a70ad61c9d1a514e
출처 데이터셋
uspto-grants-1984_06
특허 번호
US04455295

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