4-Toluenesulfonyl chloride → HCID 86723761, compound

HRID 577531Notes

Reaction equation

HRID 577531 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:17][CH:18]([CH3:20])[CH3:19])[C:5]([CH3:16])=[C:6]([CH:15]=1)[CH2:7][NH:8][CH2:9][CH:10]([O:13][CH3:14])[O:11][CH3:12].C([O-])([O-])=O.[Na+].[Na+].[S:27](Cl)([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28]>C1COCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([O:17][CH:18]([CH3:20])[CH3:19])[C:5]([CH3:16])=[C:6]([CH:15]=1)[CH2:7][N:8]([CH2:9][CH:10]([O:11][CH3:12])[O:13][CH3:14])[S:27]([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 86723759HCID 86723759, compound

Product 1

HCID 86723761HCID 86723761, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-[5-bromo-2-methyl-3-(propan-2-yloxy)benzyl]-2,2-dimethoxyethanamine (108c, 3.5 g, 10 mmol) and Na2CO3 (1.6 g, 15 mmol) in THF (40 mL) and H2O (20 mL) was added TsCl (2.0 g, 11 mmol). The reaction mixture was stirred at room temperature for 5 hours, then extracted with EtOAc (4×40 mL). The combined organic layers were washed with H2O (2×30 mL) and brine (2×100 mL), dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc=5:1) to give N-[5-bromo-2-methyl-3-(propan-2-yloxy)benzyl]-N-(2,2-dimethoxyethyl)-4-methylbenzenesulfonamide (108d, 4.7 g, 93%) as a colorless oil.

Workup

  1. extractionextracted with EtOAc (4×40 mL)
  2. washThe combined organic layers were washed with H2O (2×30 mL) and brine (2×100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography (petroleum ether/EtOAc=5:1)

Sources & evidence

ORD record
ord-831233fddd3449f28d2e49350c62250f
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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