Potassium Carbonate → 4-(4-Bromo-benzyl)-thiomorpholine 1,1-dioxide

HRID 472378

Reaction equation

HRID 472378 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]Cl)=[CH:18][CH:17]=1>CC(C)=O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:1]2[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68528p-Bromobenzyl chlorideHCID 6484228Thiomorpholine 1,1-dioxide

Product 1

HCID 523254684-(4-Bromo-benzyl)-thiomorpholine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a well stirred suspension of thiomorpholine 1,1-dioxide (0.36 g, 2.7 mmol) and potassium carbonate (0.37 g, 2.7 mmol) in acetone (5 mL) was added 1-bromo-4-chloromethyl-benzene (0.50 g, 2.4 mmol). The mixture was stirred for 48 hours at room temperature. The mixture was filtered and the volatiles were evaporated. The residue was suspended in ether (100 mL), filtered and evaporated to a solid. The material was purified via chromatography utilizing an ISCO automated purification apparatus (24 g silica gel column 10%→100% ethyl acetate in hexane). 4-(4-Bromo-benzyl)-thiomorpholine 1,1-dioxide was isolated as a white solid (0.72 g, 97%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.47 (d, J=7.6 Hz, 2H), 7.19 (d, J=7.7 Hz, 2H), 3.60 (s, 2H), 3.08-2.94 (m, 8H). MS=304, 306 (MH)+.

Workup

  1. stirringThe mixture was stirred for 48 hours at room temperature
  2. filtrationThe mixture was filtered
  3. customthe volatiles were evaporated
  4. filtrationfiltered
  5. customevaporated to a solid
  6. customThe material was purified via chromatography
  7. custompurification apparatus (24 g silica gel column 10%→100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d31aa3f94bd74546ac9e0316d120c040
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Linked notes

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