Dibenzylamine → N,N-dibenzyl-2-bromobenzenesulfonamide

HRID 915601Notes

Reaction equation

HRID 915601 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].C(N(CC)CC)C.[CH2:19]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH2:27]([N:26]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])(=[O:10])=[O:9])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7656DibenzylamineHCID 8471TriethylamineHCID 5204032-Bromobenzenesulfonyl chloride

Product 1

HCID 3731394N,N-dibenzyl-2-bromobenzenesulfonamideYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

2-Bromobenzenesulfonyl chloride (1.0 g, 3.91 mmol) and triethylamine (455 mg, 0.63 mL, 4.5 mmol) were dissolved in THF (15 mL), and the mixture was cooled to 10° C. Dibenzylamine (849 mg, 0.83 mL, 4.3 mmol) was then added dropwise. The cooling bath was removed, and the reaction mixture was stirred for 10 h at rt and then an additional 6 h at 60° C. After cooling to rt, the solvent was removed under reduced pressure, and ethyl acetate was added. The organic layer was successively washed with 1N HCl, water, semi-saturated aq Na2CO3 solution, water, and brine. After drying with Na2SO4 and filtration, the solvent was removed under reduced pressure to afford the title compound as off-white crystals (1.44 g, 88%). 1H NMR (400 MHz, CDCl3) δ 4.42 (s, 4H), 7.08 (m, 4H), 7.27 (m, 6H), 7.41 (m, 2H), 7.78 (d, 1H), 8.19 (d, 1H).

Workup

  1. customThe cooling bath was removed
  2. customan additional 6 h
  3. customat 60° C
  4. temperatureAfter cooling to rt
  5. customthe solvent was removed under reduced pressure, and ethyl acetate
  6. additionwas added
  7. washThe organic layer was successively washed with 1N HCl, water, semi-saturated aq Na2CO3 solution, water, and brine
  8. dry with materialAfter drying with Na2SO4 and filtration
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f9d57061d5ba4f5dae8ec74d4cd78720
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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