Hydrochloric Acid → HCID 178498871, 화합물

HRID 34676

반응식

HRID 34676 반응식
CO.[Na].CO[C:6](=O)[CH2:7][N:8]([CH2:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=1)C=O.[CH:21]([O:23][CH3:24])=[O:22].C[O-].[Na+].Cl.[S-:29][C:30]#[N:31].[K+]>O1CCCC1.O>[CH3:24][O:23][C:21]([C:7]1[N:8]([CH2:11][C:12]2[CH:13]=[C:14]([F:19])[CH:15]=[C:16]([F:18])[CH:17]=2)[C:30]([SH:29])=[N:31][CH:6]=1)=[O:22]

참가 물질

10

반응물 7

HCID 313Hydrochloric AcidHCID 887MethanolHCID 7865Methyl formateHCID 516872Potassium thiocyanateHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 14254152N-formyl-(3,5-difluorobenzyl)glycine methyl ester

생성물 1

HCID 178498871HCID 178498871, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Methanol (1.54 ml, 0.0381 mole) was added to a suspension of sodium (0.876 g, 0.0381 mole) in dry tetrahydrofuran and the mixture stirred for 30 minutes. A solution of N-formyl-(3,5-difluorobenzyl)glycine methyl ester (8.50 g, 0.0349 mole) prepared as above in methyl formate (6.57 ml, 0.107 mole) was added dropwise to the sodium methoxide solution with cooling at 10° to 15° C. and the resulting mixture was stirred overnight at room temperature. The solvent was removed under vacuum and the residue was diluted with 100 ml water-methanol (1:1). The solution was treated with activated carbon, filtered and cooled in ice. Hydrochloric acid (12 N, 6.4 ml) and a solution of potassium thiocyanate (4.25 g, 0.0437 mole) in a minimum amount of water were added and the resulting solution was heated at 65°-70° C. for 24 hours. The solution was treated with activated carbon, filtered, and the solvent was removed under vacuum until a precipitate formed. The mixture was cooled in ice and the product filtered and washed with a mixture of methanol-water. The product was triturated with ethanol, filtered and dried to give 1-(3,5-difluorobenzyl)-2-mercaptoimidazole-5-carboxylic acid methyl ester, m.p.: 177°-178° C. (6.75 g, 68%).

후처리

  1. temperaturewith cooling at 10° to 15° C.
  2. stirringthe resulting mixture was stirred overnight at room temperature
  3. customThe solvent was removed under vacuum
  4. additionthe residue was diluted with 100 ml water-methanol (1:1)
  5. additionThe solution was treated with activated carbon
  6. filtrationfiltered
  7. temperaturecooled in ice
  8. temperaturethe resulting solution was heated at 65°-70° C. for 24 hours
  9. additionThe solution was treated with activated carbon
  10. filtrationfiltered
  11. customthe solvent was removed under vacuum until a precipitate
  12. customformed
  13. temperatureThe mixture was cooled in ice
  14. filtrationthe product filtered
  15. washwashed with a mixture of methanol-water
  16. customThe product was triturated with ethanol
  17. filtrationfiltered
  18. customdried

출처 및 근거

ORD 기록
ord-180481be400547db9d3956d628cfa667
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04762850

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