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

HRID 1715199ノート

反応式

HRID 1715199 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
25 °C

実験手順

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 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%).

後処理

  1. addition290 g, 1 wt) was added in one portion
  2. customwas obtained
  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 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)

出典と根拠

ORDレコード
ord-01dba262d8f24a5380f0cc408abcc15c
出典データセット
uspto-grants-2010_09
特許番号
US07799815B2

反応ノート

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