N-bromobutanimide → HCID 15376566, compound

HRID 265222Notes

Reaction equation

HRID 265222 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 filtered 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. filtrationThe solution is then filtered
  4. washwashed in succession with sodium disulphide solution, sodium hydrogen carbonate solution and water
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness i.v
  7. customCrystallization of the residue from diisopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-d07f04eb8b27460dab5b58b52beb4859
Source dataset
uspto-grants-1997_07
Patent number
US05648315

Reaction notes

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