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

HRID 3620

반응식

HRID 3620 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-88c4d02c8563491e94268fb63352bd18
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733849

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