1-Bromo-3-chloropropane → 3-[(3-Chloropropyl)thio]-4-methyl-5-(4-methyl-1,3-oxazol-5-yl)-4H-1,2,4-triazole

HRID 1716437노트

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HRID 1716437 반응식
CC[O-].[Na+].[CH3:5][N:6]1[C:10]([C:11]2[O:15][CH:14]=[N:13][C:12]=2[CH3:16])=[N:9][NH:8][C:7]1=[S:17].Br[CH2:19][CH2:20][CH2:21][Cl:22]>CCO>[Cl:22][CH2:21][CH2:20][CH2:19][S:17][C:7]1[N:6]([CH3:5])[C:10]([C:11]2[O:15][CH:14]=[N:13][C:12]=2[CH3:16])=[N:9][N:8]=1

참가 물질

5

반응물 3

HCID 80061-Bromo-3-chloropropaneHCID 2723922Sodium ethoxideHCID 104202044-Methyl-3-(4-methyloxazol-5-yl)-1H-1,2,4-triazole-5(4H)-thione

생성물 1

HCID 446279943-[(3-Chloropropyl)thio]-4-methyl-5-(4-methyl-1,3-oxazol-5-yl)-4H-1,2,4-triazole

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
25 °C

실험 절차

NaOEt (21% solution in EtOH, 2.08 vol, 1.1 eq) was added to EtOH (20 vol) under nitrogen atmosphere. 4-Methyl-5-(4-methyl-1,3-oxazol-5-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (respectively a tautomeric form thereof; 290 g, 1 wt) was added in one portion and the resulting mixture stirred at 25±2° C. until a clear solution-was obtained. Then 1-bromo-3-chloropropane (0.54 vol, 1.1 eq) was added and the solution stirred at 40° C for 24 h then cooled to 25° C. After filtration water (20 vol) was added and the ethanolic phase was removed by vacuum distillation (internal temperature ˜40° C). The mixture was extracted with EtOAc (41 vol). The aqueous layer was removed and the organic phase was evaporated to dryness. Dichloromethane (4 vol) was added. The organic solution is purified through a short silica gel column (18 wt of silica), eluting with EtOAc (200 vol) to give the title compound as a solid foam (267.64 g, 66%).

후처리

  1. addition290 g, 1 wt) was added in one portion
  2. customobtained
  3. stirringthe solution stirred at 40° C for 24 h
  4. temperaturethen cooled to 25° C
  5. filtrationAfter filtration water (20 vol)
  6. additionwas added
  7. customthe ethanolic phase was removed by vacuum distillation (internal temperature ˜40° C)
  8. extractionThe mixture was extracted with EtOAc (41 vol)
  9. customThe aqueous layer was removed
  10. customthe organic phase was evaporated to dryness
  11. additionDichloromethane (4 vol) was added
  12. customThe organic solution is purified through a short silica gel column (18 wt of silica)
  13. washeluting with EtOAc (200 vol)

출처 및 근거

ORD 기록
ord-ab145bc2d62c40c9b0b13bd0a1e23116
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803820B2

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