HCID 23500268, compound → HCID 23500299, compound

HRID 1835869Notes

Reaction equation

HRID 1835869 reaction equation
C([S:20][CH2:21][CH2:22][CH2:23][S:24][CH2:25][CH2:26][CH2:27][S:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][S:37][CH2:38][CH2:39][CH2:40][S:41][CH2:42][CH2:43][CH2:44][S:45]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>FC(F)(F)C(O)=O.C(Cl)Cl>[SH:45][CH2:44][CH2:43][CH2:42][S:41][CH2:40][CH2:39][CH2:38][S:37][CH2:36][CH2:35][O:34][CH2:33][CH2:32][O:31][CH2:30][CH2:29][S:28][CH2:27][CH2:26][CH2:25][S:24][CH2:23][CH2:22][CH2:21][SH:20]

Participants

4

Reactant 1

HCID 23500268HCID 23500268, compound

Product 1

HCID 23500299HCID 23500299, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

A 2.14 g amount of 1,26 ditrityl-1,5,9,18,22,26-hexathia-12,15-dioxahexacosane was dissolved in a mixture of 9.0 ml of triflouroacetic acid and 9.0 ml of methylene chloride. About 0.7 ml of triethylenesilane was added and stirred at room temperature for a half hour. About 100 ml of methylene chloride was added to the mixture and this was washed with 50 ml of water. The organic layer was then dried with magnesium sulfate and filtered. The solvent was evaporated from filtrate and the residue was purified on silica gel using a mixture of methylene chloride and acetone (5:1 v/v). About 620 mg (58%) of 1,5,9,18,22,26-hexathia-12,15-dioxahexacosane was obtained. The preparation scheme is shown below:

Workup

  1. washthis was washed with 50 ml of water
  2. dry with materialThe organic layer was then dried with magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was evaporated from filtrate
  5. customthe residue was purified on silica gel using
  6. additiona mixture of methylene chloride and acetone (5:1 v/v)

Sources & evidence

ORD record
ord-8b057385a30748888ba81d598e331d56
Source dataset
uspto-grants-2004_08
Patent number
US06774082B2

Reaction notes

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