N-bromobutanimide → 3-(Bromomethyl)-6-phenylpyridazine

HRID 241276

Reaction equation

HRID 241276 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.C1C(=O)N([Br:21])C(=O)C1.N(C(C)(CC(C)C)C#N)=NC(C)(CC(C)C)C#N>ClCCCl>[Br:21][CH2:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 915372,2'-Azobis(2,4-dimethylvaleronitrile)2×HCID 113787443-Methyl-6-phenylpyridazine

Product 1

HCID 667174453-(Bromomethyl)-6-phenylpyridazineYield 33.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-methyl-6-phenylpyridazine (925 mg, 5.43 mmol) in 1,2-dichloroethane (28 ml) were added NBS (1.07 g, 6.01 mmol) and 2,2′-azobis(2,4-dimethylvaleronitrile) (67.3 mg, 0.271 mmol), followed by stirring at 80° C. for 1 hour. During the reaction, 2,2′-azobis(2,4-dimethylvaleronitrile)(134 mg, 0.540 mmol) was additionally added in two portions. After completion of the reaction, the reaction solution was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=5:1→0:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (449 mg) as a slightly brown solid. (Yield: 33%)

Workup

  1. additionwas additionally added in two portions
  2. customAfter completion of the reaction
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. additioncontaining the desired compound
  5. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-9764fadbf8674d9f85871f740dd60b76
Source dataset
uspto-grants-2014_02
Patent number
US08648097B2

Linked notes

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