N-bromobutanimide → HCID 58504032, compound

HRID 2407721Notes

Reaction equation

HRID 2407721 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:17][CH2:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 7454275HCID 7454275, compound

Product 1

HCID 58504032HCID 58504032, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the compound prepared in Example 151 (3.50 g) and N-bromosuccinimide (2.66 g) and benzoyl peroxide (0.362 g) in carbon tetrachloride (80 mL) was heated at 90° C. for 18 hours. The mixture was partitioned between a saturated aqueous sodium bicarbonate solution and dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain the title compound (4.70 g) having the following physical data.

Workup

  1. customThe mixture was partitioned between a saturated aqueous sodium bicarbonate solution and dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-766f9591cd0c43ad969e288cd38969f1
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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