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

HRID 631085Notes

Reaction equation

HRID 631085 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-91900afcaa7c4a569d0e39a61480e7e0
Source dataset
uspto-grants-2016_04
Patent number
US09320734B2

Reaction notes

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