N-bromobutanimide → HCID 67626298, compound

HRID 1966Notes

Reaction equation

HRID 1966 reaction equation
[C:1]([O:4][C:5]1[C:6]([Cl:22])=[CH:7][C:8]([Cl:21])=[C:9]([N:11]2[C:19](=[O:20])[N:14]3[CH2:15][CH2:16][CH2:17][CH2:18][C:13]3=[N:12]2)[CH:10]=1)(=[O:3])[CH3:2].[Br:23]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[C:6]([Cl:22])=[CH:7][C:8]([Cl:21])=[C:9]([N:11]2[C:19](=[O:20])[N:14]3[CH2:15][CH2:16][CH2:17][CH:18]([Br:23])[C:13]3=[N:12]2)[CH:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67626138HCID 67626138, compound

Product 1

HCID 67626298HCID 67626298, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 3.55 g (10.4 mmol) of 5,6,7,8-tetrahydro-2-(5-acetyloxy-2,4-dichlorophenyl)-1,2,4-triazolo[4,3-α]pyridin-3(2H)-one in 100 mL of carbon tetrachloride was added 2.03 g (11.4 mmol) of N-bromosuccinimide at room temperature. The mixture was warmed under reflux by irradiating with a sun lamp for 3h. The mixture was cooled to room temperature and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel, eluting with a 1:1 v:v mixture of ethyl acetate and n-hexane to give 4.10 g of the title product of Step 1 as a white solid, m.p.: 75°-83° C.; 1H NMR (CDCl3, 300 MHz) δ 7.6 (s,1H), 7.35 (s,1H), 5.25 (m,1H), 4.0 (m,1H), 3.6 (m,1H), 2.75 (s,3H), 2.5-1.9 (m,4H).

Workup

  1. temperatureThe mixture was warmed
  2. temperatureunder reflux
  3. customby irradiating with a sun lamp for 3h
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography over silica gel
  6. washeluting with a 1:1 v
  7. additionv mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-8a4b58ae25a9460d8b441c80118dd2e8
Source dataset
uspto-grants-1998_03
Patent number
US05728651

Reaction notes

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