4-Toluenesulfonyl chloride → HCID 23516613, compound

HRID 1835868Notes

Reaction equation

HRID 1835868 reaction equation
C(N([CH2:6][CH3:7])CC)C.[CH2:8]([OH:30])[CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][S:16][CH2:17][CH2:18][CH2:19][S:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][OH:29].[C:31]1([CH3:41])[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(Cl)Cl>[S:37]([O:30][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][S:16][CH2:17][CH2:18][CH2:19][S:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][S:37]([C:7]1[CH:6]=[CH:36][C:31]([CH3:41])=[CH:32][CH:33]=1)(=[O:39])=[O:38])([C:34]1[CH:35]=[CH:36][C:31]([CH3:41])=[CH:32][CH:33]=1)(=[O:39])=[O:38]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 23500256HCID 23500256, compound

Product 1

HCID 23516613HCID 23516613, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 20 ml of methylene chloride and 5.1 g of triethylamine was added 5.6 g of 9,13-dithia-3,6,16,19-tetraoxaheneicosane 1,21-diol. Then 6.1 g of p-toluenesulfonyl chloride at 0° to 5° C. in 20 ml of methylene chloride was added dropwise. The mixture was stirred overnight at room temperature and then was washed with 50 ml of water. The organic layer was dried over MgSO4. After filtration, the solvent from the filtrate was evaporated and the residue was purified using silica gel column chromatography (CH2Cl2/CH3COCH3) (50:1 v/v). About 8 g (78%) of 9,13-dithia-3,6,16,19-tetraoxaheneicosane-1,21-diol ditosylate was collected. The process step for obtaining this composition is shown schematically below:

Workup

  1. washwas washed with 50 ml of water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationAfter filtration
  4. customthe solvent from the filtrate was evaporated
  5. customthe residue was purified
  6. customAbout 8 g (78%) of 9,13-dithia-3,6,16,19-tetraoxaheneicosane-1,21-diol ditosylate was collected
  7. customThe process step for obtaining this composition

Sources & evidence

ORD record
ord-4c808629f9bd42f48120607167d3bc88
Source dataset
uspto-grants-2004_08
Patent number
US06774082B2

Reaction notes

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