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Benzaldehyde → 2-Hydroxy-3-phenylpyrazine

HRID 1995057
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HRID 1995057 반응식
[C-:1]#[N:2].[K+].[Cl-].[NH4+:5].[CH:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl.[CH:15]([CH:17]=O)=O.[OH-:19].[Na+]>C(Cl)Cl.CO.O>[C:7]1([C:6]2[C:1](=[O:19])[NH:2][CH:15]=[CH:17][N:5]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1
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참가 물질

10

반응물 6

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 7860GlyoxalHCID 9032Potassium CyanideHCID 14798Sodium HydroxideHCID 25517Ammonium Chloride

생성물 1

HCID 1559662-Hydroxy-3-phenylpyrazine

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

To a stirred solution of 0.3 mol. of potassium cyanide and 0.3 mol. of ammonium chloride in 100 ml. of water is added a solution of 0.3 mol. of benzaldehyde (Aldrich Chemical Co.) in 100 ml. of methanol. The reaction mixture is stirred at 25° C. for 6.0 hr. The oil layer is isolated and dissolved in methylene chloride. The solution is washed with water, dried and evaporated to give a brown oil. The oil is stirred with 150 ml. of concentrated hydrochloric acid for 1.0 hr. at 45° C. to precipitate phenylglycinamide hydrochloride. The precipitate is dissolved in 120 ml. of water stirred and cooled to 2° C. A solution of 4.8 g. (0.03 mol.) of 40% aqueous glyoxal is added, followed by dropwise addition of 6.0 ml. of 10 N sodium hydroxide. The reaction mixture is stirred for 5.0 hr. at 2° C. and then filtered. The filtrate is acidified to pH 6 with 3.0 ml. of 10 N hydrochloric acid and the precipitate of title compound is collected by filtration.

후처리

  1. customThe oil layer is isolated
  2. washThe solution is washed with water
  3. customdried
  4. customevaporated
  5. customto give a brown oil
  6. stirringThe oil is stirred with 150 ml
  7. customat 45° C. to precipitate phenylglycinamide hydrochloride
  8. dissolutionThe precipitate is dissolved in 120 ml
  9. stirringof water stirred
  10. temperaturecooled to 2° C
  11. additionfollowed by dropwise addition of 6.0 ml
  12. stirringThe reaction mixture is stirred for 5.0 hr
  13. filtrationat 2° C. and then filtered
  14. filtrationof 10 N hydrochloric acid and the precipitate of title compound is collected by filtration

출처 및 근거

ORD 기록
ord-b967161755a14de985ee6f8a78251f6e
출처 데이터셋
uspto-grants-1983_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04402958

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