Propargyl bromide → 2-(t-Butyl)-5-(2,6-dichloro-4-pyridyl)-4-propargyl-1,2,4-triazolin-3-one

HRID 3620

反応式

HRID 3620 の反応式
[C:1]([N:5]1[C:9](=[O:10])[NH:8][C:7]([C:11]2[CH:16]=[C:15]([Cl:17])[N:14]=[C:13]([Cl:18])[CH:12]=2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:25](Br)[C:26]#[CH:27]>O.C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([N:5]1[C:9](=[O:10])[N:8]([CH2:27][C:26]#[CH:25])[C:7]([C:11]2[CH:12]=[C:13]([Cl:18])[N:14]=[C:15]([Cl:17])[CH:16]=2)=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 1363512752-(t-Butyl)-5-(2,6-dichloro-4-pyridyl)-1,2,4-triazolin-3-one

生成物 1

HCID 867523412-(t-Butyl)-5-(2,6-dichloro-4-pyridyl)-4-propargyl-1,2,4-triazolin-3-one

試薬・触媒・溶媒 3

HCID 962Water触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

To 2.06 g (7.2 mmol) of crude 2-(t-butyl)-5-(2,6-dichloro-4-pyridyl)-1,2,4-triazolin-3-one were added 30 mL of ethyl acetate, 1 drop of water, and 1.00 g (7.30 mmol) of powdered K2CO3. The mixture was heated to reflux and after 15 min 1.10 g (7.4 mmol) of an 80% by weight solution of propargyl bromide in toluene was added. Refluxing was continued for 2.5 hours. The mixture was cooled, diluted with 175 mL of ethyl acetate, washed with 25 mL of water, and dried over MgSO4. Reomoval of the solvent left 2.18 g of crude product as a reddish solid. The crude product was combined with 0.69 g of material from another run and purified by flash chromatography first on a silica gel column and then on a neutral alumina column eluted portionwise in both cases with ether hexane mixtures containing successively greater percentages of ether to afford 0.97 g of 2-(t-butyl)-5-(2,6-dichloro-4-pyridyl)-4-propargyl-1,2,4-triazolin-3-one (Compound 1) as a white solid, m.p. 107°-109° C. 1H-NMR (CDCl3)∂1.6 (9H,s), 2.45 (1H,t), 4.6 (2H,d), 7.75 (2H,s).

後処理

  1. temperatureThe mixture was heated
  2. additionwas added
  3. temperatureRefluxing
  4. temperatureThe mixture was cooled
  5. washwashed with 25 mL of water
  6. dry with materialdried over MgSO4
  7. waitReomoval of the solvent left 2.18 g of crude product as a reddish solid
  8. custompurified by flash chromatography first on a silica gel column
  9. washon a neutral alumina column eluted portionwise in both cases with ether hexane mixtures
  10. additioncontaining successively greater percentages of ether

出典と根拠

ORDレコード
ord-88c4d02c8563491e94268fb63352bd18
出典データセット
uspto-grants-1998_03
特許番号
US05733849

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