Sodium Chloride → HCID 11584206, compound

HRID 1251309Notes

Reaction equation

HRID 1251309 reaction equation
Cl.[CH2:2]([N:9]([CH2:23][CH2:24][CH2:25][NH:26][S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH2:10][CH2:11][CH2:12][NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].[Na+].[Cl-]>C(Cl)Cl>[CH2:2]([N:9]([CH2:10][CH2:11][CH2:12][NH:13][S:14]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)(=[O:15])=[O:16])[CH2:23][CH2:24][CH2:25][NH:26][S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:29])=[O:28])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 11606283HCID 11606283, compound

Product 1

HCID 11584206HCID 11584206, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Free base. In a round-bottomed flask equipped with a magnetic stir bar, 6.51 g (12.1 mmol) of N-benzylbis(3-benzenesulfonamidopropyl)amine hydrochloride, 40 mL of CH2Cl2, 15 mL of a solution of 1 N aq. NaOH and 15 mL of saturated aq. NaCl were combined. After stirring vigorously for 30 min, the layers were separated and the organic portion dried (MgSO4). Removal of the drying agent by filtration, concentration of the filtrate by rotary evaporation and further drying under vacuum (0.4 mm, 45° C.) for 24 h afforded 5.96 g (98%) of N-benzylbis (3-benzenesulfonamidopropyl)amine as a thick colorless oil. TLC (silica) : Rf=0.21, 1:1 (v/v) ethyl acetate:hexane. 1H NMR (CDCl3/TMS) δ7.82 (d, 4 H, J=7 Hz,SO2ArH2,6), 7.51 (m, 6 H, SO2ArH3,4,5), 7.22 (m, 3 H, BnArH2,4,6), 7.16 (m, 2 H, BnArH3,5), 5.9 (br, 2 H, SO2NH) 3.40 (s, 2 H, PhCH2N), 2.92 (t, 4 H, SO2NCH2CH2), 2.38 (t, 4 H, BnCH2CH2), 1.62 (quint, 4 H, NCH2CH2CH2N) 13 C NMR (CDCl3) δ139.9, 138.2, 132.4, 129.0, 128.4, 127.2, 126.9, 58.7, 51.8, 42.2, 26.1. IR (NaCl plate, cm−1) 3277 (br), 3061 (w), 1446 (s), 1325 (s), 1160 (s), 1093 (s).

Workup

  1. customIn a round-bottomed flask equipped with a magnetic stir bar
  2. customthe layers were separated
  3. dry with materialthe organic portion dried (MgSO4)
  4. customRemoval of the drying agent
  5. filtrationby filtration, concentration of the filtrate
  6. customby rotary evaporation
  7. customfurther drying under vacuum (0.4 mm, 45° C.) for 24 h

Sources & evidence

ORD record
ord-d791788fd9974b1b955d1bbb8f607aa6
Source dataset
uspto-grants-2002_01
Patent number
US06342492B1

Reaction notes

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