Methylamine → 4-dodecyl-N-(5-(5-(methylamino)pentyl)-1,3,4-thiadiazol-2-yl)benzenesulfonamide

HRID 1854304Notes

Reaction equation

HRID 1854304 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[S:11][C:10]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[N:9][N:8]=1.[CH3:34][NH2:35].C([O-])([O-])=O.[K+].[K+]>CCOCC>[CH2:22]([C:19]1[CH:20]=[CH:21][C:16]([S:13]([NH:12][C:10]2[S:11][C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:35][CH3:34])=[N:8][N:9]=2)(=[O:15])=[O:14])=[CH:17][CH:18]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 66642947N-(5-(5-Bromopentyl)-1,3,4-thiadiazol-2-yl)-4-dodecylbenzenesulfonamide

Product 1

HCID 583025024-dodecyl-N-(5-(5-(methylamino)pentyl)-1,3,4-thiadiazol-2-yl)benzenesulfonamideYield 61%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of N-(5-(5-bromopentyl)-1,3,4-thiadiazol-2-yl)-4-dodecylbenzenesulfonamide (100 mg, 0.18 mmol), CH3NH2 (0.42 mL, 40% solution in water, 5.4 mmol), K2CO3 (25 mg, 0.18 mmol), and KI (30 mg, 0.18 mmol) was heated at reflux for 2 d. The reaction mixture was diluted with ether (50 mL), washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated. The crude product was purified by chromatography over silica gel 60 (70-230 mesh) eluted with CH2Cl2:methanol 2:3 to give the product as a solid, mp 158-160° C., in 61% yield (56 mg, 0.11 mmol). 1H NMR (300 MHz, CDCl3) δ 0.87 (t, 3, J=7.2 Hz), 1.25-1.36 (m, 18), 1.53-1.67 (m, 8), 2.57-2.61 (m, 5), 2.68 (t, 2, J=7.2 Hz), 2.96 (t, 2, J=6.9 Hz), 7.20 (d, 2, J=8.4 Hz), 7.75 (d, 2, J=8.1 Hz); 13C NMR (75 MHz, CDCl3) δ 14.1, 22.7, 25.5, 28.3, 29.3, 29.4, 29.5, 29.7, 30.5, 31.2, 31.9, 33.1, 35.8, 60.0, 126.1, 128.5, 140.7, 146.7, 163.7, 170.7; HRMS (ESI+, m/z) calculated for C26H45N4O2S2 509.2984, observed 509.2972 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 d
  3. washwashed with brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography over silica gel 60 (70-230 mesh)
  8. washeluted with CH2Cl2:methanol 2:3

Sources & evidence

ORD record
ord-29f8e5bc58224906b1d7574087b82b5c
Source dataset
uspto-grants-2015_02
Patent number
US08962663B2

Reaction notes

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