Water → HCID 10732285, compound

HRID 1599391Notes

Reaction equation

HRID 1599391 reaction equation
[Cl:1][C:2]1[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][C:12]=2[CH3:13])=[N:5][S:4][N:3]=1.[Br:14]N1C(=O)CCC1=O.O.C([O-])([O-])=O.[K+].[K+]>ClC(Cl)(Cl)Cl>[Br:14][CH2:13][C:12]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[C:6]1[C:2]([Cl:1])=[N:3][S:4][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 190753933-(4-Chloro-1,2,5-thiadiazol-3-yl)-4-methylpyridine

Product 1

HCID 10732285HCID 10732285, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 3-(3-chloro-1,2,5-thiadiazol-4-yl)-4-methylpyridine (0.63 g, 3 mmol) in tetrachloromethane (50 ml) was added under nitrogen, N-bromosuccinimide (0.80 g, 4.5 mmol) and α,α-azoisobutyronitril (80 mg, 0.5 mmol). The reaction mixture was stirred at 75° C. overnight. Water (50 ml) was added and after basifying with K2CO3 the reaction mixture was extracted with methylene chloride (3×100 ml). The organic phases were dried (MgSO4) and evaporated. The residue contained a mixture of starting material, the monobromo and the dibromo product. Separation by column chromatography, eluent: ethyl acetate/methylene chloride: 1/10, gave the title compound in 180 mg (20%) yield.

Workup

  1. extractionwas extracted with methylene chloride (3×100 ml)
  2. dry with materialThe organic phases were dried (MgSO4)
  3. customevaporated
  4. additiona mixture of starting material
  5. customSeparation by column chromatography, eluent

Sources & evidence

ORD record
ord-2a5dc389d0b641b7a932bd79873e56a9
Source dataset
uspto-grants-1998_04
Patent number
US05741788

Reaction notes

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