4-Aminophenylacetic acid → 4-Mercaptophenylacetic acid

HRID 268032

반응식

HRID 268032 반응식
N([O-])=O.[Na+].N[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1.CCOC([S-])=[S:20].[K+]>O.Cl>[SH:20][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1

참가 물질

6

반응물 3

HCID 145334-Aminophenylacetic acidHCID 2735045Potassium ethylxanthateHCID 23668193Sodium Nitrite

생성물 1

HCID 33905114-Mercaptophenylacetic acid

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매2회HCID 962Water용매3회

실험 절차

A solution of 27.6 g of sodium nitrite in 200 cc of water is added dropwise at 0°, while stirring, to a suspension of 60.4 g of 4-aminophenyl-acetic acid in 200 cc of water and 80 cc of concentrated hydrochloric acid. After the addition is complete, the reaction mixture is stirred at the same temperature for a further 45 minutes. This cold diazonium salt solution is then added dropwise at room temperature to a mixture of 74 g of potassiumethyl xanthogenate, 120 cc of water and 300 cc of a 2 N soda solution, and heating is effected to 45° until gas evolution stops. The mixture is subsequently cooled to room temperature, the pH is adjusted to 1 with concentrated hydrochloric acid and the oiled xanthogenate ester is extracted with ether. After removing the solvent by distillation, the ester is taken up in 500 cc of ethanol, a solution of 90 g of potassium hydroxide in 500 cc of water is added and boiling at reflux is effected for 20 hours. The major portion of the ethanol is subsquently removed by the distillation at reduced pressure, the aqueous phase is cooled with ice, rendered acid with concentrated hydrochloric acid while stirring well, and extracted with ether. The ether extract is dried over sodium sulphate, the solvent is removed by distillation, whereby 4-mercapto-phenylacetic acid crystallizes. After recrystallization from ether/pentane, the acid has a M.P. of 101° to 103°.

후처리

  1. additionAfter the addition
  2. temperatureheating
  3. customis effected to 45° until gas evolution
  4. extractionthe oiled xanthogenate ester is extracted with ether
  5. customAfter removing the solvent
  6. distillationby distillation
  7. additiona solution of 90 g of potassium hydroxide in 500 cc of water is added
  8. temperatureat reflux
  9. waitis effected for 20 hours
  10. customThe major portion of the ethanol is subsquently removed by the distillation at reduced pressure
  11. temperaturethe aqueous phase is cooled with ice
  12. stirringwhile stirring well
  13. extractionextracted with ether
  14. extractionThe ether extract
  15. dry with materialis dried over sodium sulphate
  16. customthe solvent is removed by distillation, whereby 4-mercapto-phenylacetic acid
  17. customcrystallizes
  18. customAfter recrystallization from ether/pentane

출처 및 근거

ORD 기록
ord-b06a6737f1ae4949b20e0fee470de17b
출처 데이터셋
uspto-grants-1976_03
특허 번호
US03946036

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