Glycine → N-(2-benzoylmercapto-p-chlorophenylacetyl)glycine

HRID 918578노트

반응식

HRID 918578 반응식
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].Br[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[CH2:16][C:17](Cl)=[O:18].[C:20]([OH:28])(=[S:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[C:20]([S:27][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[CH2:16][C:17]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:18])(=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

5

반응물 4

HCID 750GlycineHCID 14798Sodium HydroxideHCID 197942342-Bromo-p-chlorophenylacetyl chlorideHCID 178526132HCID 178526132, 화합물

생성물 1

HCID 53670751N-(2-benzoylmercapto-p-chlorophenylacetyl)glycine수율 76.9%

실험 절차

4.9g (0.065 mol) of glycine was dissolved in 250 ml of 0.5 N--NaOH and then to the solution was added dropwise 14.6g (0.054 mol) of 2-bromo-p-chlorophenylacetyl chloride over 1 hour while stirring and cooling with a freezing mixture. After completion of the addition, the reaction mixture was stirred at room temperature for an additional 2 hours. During stirring, the pH of the mixture was adjusted to 8. The filtrate which had been prepared by dissolving 11.6g (0.08 mol) of thiobenzoic acid in 40 ml of 2N--KOH and filtering the solution to remove undissolved substances was added to the reaction mixture followed by stirring at room temperature overnight. The next morning, the mixture was acidified with hydrochloric acid while ice-cooling to precipitate crystals. These crystals were recovered by filtration, washing with water and washing with benzene to give 15.1g of crude N-(2-benzoylmercapto-p-chlorophenylacetyl)glycine. The product had a melting point of 158° - 159°C after recrystallization from ethyl acetate-benzene. 11.0g (0.03 mol) of N-(2-benzoylmercapto-p-chlorophenylacetyl)glycine was dissolved in 75 ml of concentrated aqueous ammonia followed by stirring at room temperature for 1 hour. After removal of benzamide by extraction with ethyl acetate, the resulting aqueous layer was treated in a similar manner in accordance with Example I to give 6.0g of N-(2-mercapto-p-chlorophenylacetyl)glycine, ClC6H4CH(SH)--CONHCH2COOH. (m.p. 148° - 149°C, Purity; 100 % (iodometry))

후처리

  1. temperaturecooling with a freezing mixture
  2. additionAfter completion of the addition
  3. stirringthe reaction mixture was stirred at room temperature for an additional 2 hours
  4. stirringDuring stirring
  5. customThe filtrate which had been prepared
  6. filtrationKOH and filtering the solution
  7. customto remove undissolved substances
  8. additionwas added to the reaction mixture
  9. stirringby stirring at room temperature overnight
  10. temperaturecooling
  11. customto precipitate crystals
  12. filtrationThese crystals were recovered by filtration
  13. washwashing with water
  14. washwashing with benzene

출처 및 근거

ORD 기록
ord-655ac66f12e2428887263fb69dbd0c77
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03971828

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