N-bromobutanimide → HCID 15376566, compound

HRID 1979104Notes

Reaction equation

HRID 1979104 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[C:16]([O:18][CH3:19])=[O:17])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:20]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([CH2:15][Br:20])[CH:12]=[CH:11][C:10]=1[C:16]([O:18][CH3:19])=[O:17])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 21993067HCID 21993067, compound

Product 1

HCID 15376566HCID 15376566, compoundYield 59.9%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 54.8 g (192 mmol) of N-tert-butyl-2-methoxycarbonyl-5-methylbenzenesulfonamide in 420 ml of tetrachloromethane is heated at reflux for 6-8 h under a nitrogen protective-gas atmosphere, following addition of 36 g (202 mmol) of N-bromosuccinimide and 0.5 g of azobisisobutyronitrile (AIBN) with simultaneous irradiation with a daylight lamp. The solution is then filterd and then washed in succession with sodium disulphide solution, sodium hydrogen carbonate solution and water, dried over Na2SO4 and evaporated to dryness i.v. Crystallization of the residue from diisopropyl ether/ethyl acetate yields 41.9 g (57%) of N-tert-butyl-5-bromomethyl-2-methoxycarbonylbenzenesulfonamide of mp. 88-90° C.

Workup

  1. temperatureat reflux for 6-8 h under a nitrogen protective-gas atmosphere
  2. customwith simultaneous irradiation with a daylight lamp
  3. washwashed in succession with sodium disulphide solution, sodium hydrogen carbonate solution and water
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness i.v
  6. customCrystallization of the residue from diisopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-2be1ac76d049462f8c4256214e357b23
Source dataset
uspto-grants-2001_05
Patent number
US06239306B1

Reaction notes

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