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Pyridine → N-(2-(6-(methoxymethoxy)-2,2,7,8-tetramethylchroman-5-yl)ethyl)-4-methylbenzenesulfonamide

HRID 1021192
Notes
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Reaction equation

HRID 1021192 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([CH2:19][CH2:20][NH2:21])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH3:18])([CH3:17])[CH2:9][CH2:8]2.[S:22](Cl)([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)(=[O:24])=[O:23].N1C=CC=CC=1>C1COCC1.CCOC(C)=O>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([CH2:19][CH2:20][NH:21][S:22]([C:25]2[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=2)(=[O:24])=[O:23])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH3:18])([CH3:17])[CH2:9][CH2:8]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 671597262-(6-(Methoxymethoxy)-2,2,7,8-tetramethylchroman-5-yl)ethanamine

Product 1

HCID 67159548N-(2-(6-(methoxymethoxy)-2,2,7,8-tetramethylchroman-5-yl)ethyl)-4-methylbenzenesulfonamideYield 37.2%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(6-(methoxymethoxy)-2,2,7,8-tetramethylchroman-5-yl)ethanamine (450 mg, 1.8 mmol) in THF (4.2 mL) at 23° C. was added tosyl chloride (390 mg, 2.0 mmol) and pyridine (270 μL, 3.4 mmol). The reaction mixture was stirred at room temperature for 45 min, diluted in 50 mL EtOAc, washed with 1 M aqueous citric acid (2×25 mL) and brine (1×25 mL). The remained organics were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (gradient elution 5→35% EtOAc/Heptane) to produce 300 mg N-(2-(6-(methoxymethoxy)-2,2,7,8-tetramethylchroman-5-yl)ethyl)-4-methylbenzenesulfonamide. 1H NMR (CDCl3, 400 MHz) 7.48 (d, 2H), 7.09 (m, 8H), 5.20 (s, 1H), 4.82 (s, 2H), 3.55 (s, 3H), 3.10 (q, 2H), 2.70 (t, 2H), 2.45 (t, 2H) 2.35 (s, 3H), 2.11 (s, 3H), 2.04 (s, 3H), 1.65 (t, 2H), 1.20 (s, 6H) ppm.

Workup

  1. washwashed with 1 M aqueous citric acid (2×25 mL) and brine (1×25 mL)
  2. dry with materialThe remained organics were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (gradient elution 5→35% EtOAc/Heptane)

Sources & evidence

ORD record
ord-e19dfe886ef64cabb027119a78c71cc6
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08716527B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes