N-bromobutanimide → HCID 53315308, compound

HRID 1896222Notes

Reaction equation

HRID 1896222 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([N:7]2[C:11](=[O:12])[CH:10]=[CH:9][S:8]2)=[CH:3][CH:2]=1.[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:14][CH2:13][C:1]1[CH:2]=[CH:3][C:4]([N:7]2[C:11](=[O:12])[CH:10]=[CH:9][S:8]2)=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 12032054HCID 12032054, compound

Product 1

HCID 53315308HCID 53315308, compoundYield 104.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Catalytic amount of benzoyl peroxide (4 mg) was added to a solution of 2-p-tolylisothiazol-3-one 30 (123 mg, 0.643 mmol), and N-bromosuccinimide (121 mg, 0.673 mmol) in carbon tetrachloride (8 mL), which was refluxed for 2 h and then cooled to room temperature. Solvent was evaporated under low pressure and the residue was purified by flash silica gel column chromatography (methylene chloride:methanol=50:1 to 20:1), afforded the compound 31 (182 mg, 93%). 1H-NMR (CDCl3, 300 MHz) δ 4.50 (s, 2H), 6.33 (d, J=6.3 Hz, 1H), 7.47 (d, J=8.4 Hz, 2H), 7.59 (d, J=8.4 Hz, 2H), 8.16 (d, J=6.3 Hz, 1H). HRMS: calculated for C10H9NOSBr (M+H)+269.9588. Found 269.9593.

Workup

  1. temperaturewas refluxed for 2 h
  2. customSolvent was evaporated under low pressure
  3. customthe residue was purified by flash silica gel column chromatography (methylene chloride:methanol=50:1 to 20:1)

Sources & evidence

ORD record
ord-56343417800e4d778807e017edec6de4
Source dataset
uspto-grants-2013_08
Patent number
US08518957B2

Reaction notes

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