Azobisisobutyronitrile → HCID 25184799, compound

HRID 2384512Notes

Reaction equation

HRID 2384512 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:14]([F:15])=[C:13]([CH2:16][CH3:17])[N:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClC(Cl)C>[Br:18][CH:16]([C:13]1[C:14]([F:15])=[C:9]([S:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:10]=[CH:11][N:12]=1)[CH3:17]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 675424934-[(4-Chlorophenyl)sulfanyl]-6-ethyl-5-fluoropyrimidine

Product 1

HCID 25184799HCID 25184799, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

131 g of 4-(4-chloro-phenylsulfanyl)-6-ethyl-5-fluoropyrimidine, 103.8 g of N-bromosuccinimide and 7.98 g of azobisisobutyronitrile were dissolved in 850 ml of dichloroethane. The resulting mixture was refluxed for 2 hours, cooled to room temperature, and washed successively with 800 ml of water, 50 g of sodium metabisulfite in 950 ml of water and 500 ml of brine. The resulting solution was concentrated under a reduced pressure and crystallized at 5° C. in 391 ml of isopropanol to obtain the white compound, and the compound was washed with 50 ml of isopropanol at 5° C. to obtain the white title compound (150.7 g, yield: 89%).

Workup

  1. temperatureThe resulting mixture was refluxed for 2 hours
  2. washwashed successively with 800 ml of water, 50 g of sodium metabisulfite in 950 ml of water and 500 ml of brine
  3. concentrationThe resulting solution was concentrated under a reduced pressure
  4. customcrystallized at 5° C. in 391 ml of isopropanol
  5. customto obtain the white compound
  6. washthe compound was washed with 50 ml of isopropanol at 5° C.

Sources & evidence

ORD record
ord-70aee4bdaa6f4061a20b5013995537d6
Source dataset
uspto-grants-2012_09
Patent number
US08263769B2

Reaction notes

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