N-bromobutanimide → HCID 18942783, compound

HRID 355517Notes

Reaction equation

HRID 355517 reaction equation
[Br:1]N1C(=O)CCC1=O.[O:9]([C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[CH3:26])[C:20]([NH2:22])=[O:21])[Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]>C(Cl)(Cl)(Cl)Cl>[O:9]([C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[CH2:26][Br:1])[C:20]([NH2:22])=[O:21])[Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18942782HCID 18942782, compound2×

Product 1

HCID 18942783HCID 18942783, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (NBS) (0.507 g, 2.85 mmol) was added to a solution of 3-t-butyldimethylsiloxy-4-methyl benzamide (Compound 7.1) in 30 mL CCl4. The mixture was irradiated with a 275 W sunlamp (Sears, #34-7105) at 60° C. Each irradiation took 10 minutes followed by 10 minutes to let the lamp cool down. It took 2 hours of irradiation over a period of 4 hours to complete the reaction. After the solvent was removed at reduced pressure, the residue was subjected to flash silica gel chromatography to yield the product as a white solid (0146 g, y=81.7%). 1H NMR (CDCl3) δ0.318(s,6H), 1.05(s,9H), 4.51(s,2H), 6.10(b,2H), 7.25(d,J=7.8 Hz,1H), 7.32(s,1H), 7.39(d,J=7.9 Hz,1H); 13 C NMR (CDCl3) δ-4.08, 18.28, 25.76, 27.87, 117.99, 118.07, 119.49, 131.23, 132.54, 134.97, 168.46.

Workup

  1. customThe mixture was irradiated with a 275 W sunlamp (Sears, #34-7105) at 60° C
  2. customEach irradiation
  3. waitfollowed by 10 minutes
  4. temperaturecool down
  5. customIt took 2 hours of irradiation over a period of 4 hours
  6. customthe reaction
  7. customAfter the solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-df00efb9655645208bf8593fc8b71fcc
Source dataset
uspto-grants-1998_11
Patent number
US05831073

Reaction notes

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