Dibenzylamine → HCID 44550989, compound

HRID 2238435Notes

Reaction equation

HRID 2238435 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12](Cl)(=[O:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[CH2:16]([NH:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(CC)CC>C1COCC1>[CH2:24]([N:23]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[S:12]([C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=2)[CH:9]=1)(=[O:14])=[O:13])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7656DibenzylamineHCID 8471TriethylamineHCID 13742644127769-56-6

Product 1

HCID 44550989HCID 44550989, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 207 (1.50 g, 4.92 mmol), dibenzylamine (1.45 g, 7.38 mmol), and Et3N (0.75 g, 7.38 mmol) in THF (15 mL) was stirred at room temperature for 48 h. The solvents were evaporated under reduced pressure and the residue was extracted with EtOAc. The EtOAc extracts were washed with water and brine, then dried and evaporated. The residue was purified by chromatography on silica gel eluting with petroleum ether/EtOAc (95:5 then 1:1) to give N,N-dibenzyl-7-bromo-2-naphthalenesulfonamide (208) (2.11 g, 92%). A sample was recrystallised from petroleum ether/EtOAc as colorless crystals: mp 127-129° C.; 1H NMR (CDCl3) δ 8.25 (d, J=1.4 Hz, 1H), 8.05 (d, J=1.6 Hz, 1H), 7.91 (d, J=8.7 Hz, 1H), 7.79 (dd, J1=8.6, 1.8 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.71 (dd, J=8.8, 1.9 Hz, 1H), 7.22-7.15 (m, 6H), 7.09-7.04 (m, 4H), 4.39 (s, 4H); 13C NMR δ 138.9, 135.4, 133.3, 133.0, 132.1, 131.2, 129.4, 129.3, 128.6, 128.5, 127.8, 127.3, 123.0, 121.6, 50.6. Anal. (C24H20BrNO2S. 1/10Bn2NH) C, H, N.

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. extractionthe residue was extracted with EtOAc
  3. washThe EtOAc extracts were washed with water and brine
  4. customdried
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel eluting with petroleum ether/EtOAc (95:5

Sources & evidence

ORD record
ord-5018dd644bbc49cc8a658948f03fbc55
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

Loading…