Water → HCID 22601925, compound

HRID 2308389Notes

Reaction equation

HRID 2308389 reaction equation
C(N(CC)CC)C.Cl[CH2:9][CH2:10][C:11]([S:13][CH2:14][CH:15]1[S:19][CH:18]([CH2:20][S:21][C:22](=[O:26])[CH2:23][CH2:24]Cl)[CH2:17][S:16]1)=[O:12].O.C1(C)C=CC=CC=1>CC(C)=O>[C:11]([S:13][CH2:14][CH:15]1[S:19][CH:18]([CH2:20][S:21][C:22](=[O:26])[CH:23]=[CH2:24])[CH2:17][S:16]1)(=[O:12])[CH:10]=[CH2:9]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 8471TriethylamineHCID 22602103HCID 22602103, compound

Product 1

HCID 22601925HCID 22601925, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Next, 40.0 g (0.39 mol) of triethylamine was added dropwise to a solution of 52.1 g of 2,4-bis(3-chloropropionylthiomethyl)-1,3-dithiolan prepared above and dissolved in 195 g of acetone at 2 to 50° C. in 1 hour. They were allowed to react at the same temperature for 1.5 hours, with stirring, to which 520 g of water was added. The resultant mixture was treated with 520 g of toluene to extract the reaction product. The extract organic phase (toluene solution) was washed with water until the aqueous phase turned neutral. Then, the organic phase was separated out, incorporated with 0.12 g of 4-methoxyphenol as a polymerization inhibitor, and distilled under a vacuum to be concentrated while removing toluene, to obtain a lightly yellowish, transparent liquid as the crude product. The crude product thus prepared was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate mixture), to obtain 24.6 g (0.10 mol) of 2,4-bis(acryloylthiomethyl)-1,3-dithiolan.

Workup

  1. customprepared above and
  2. customto react at the same temperature for 1.5 hours
  3. additionwas added
  4. extractionto extract the reaction product
  5. washThe extract organic phase (toluene solution) was washed with water until the aqueous phase
  6. customThen, the organic phase was separated out, incorporated with 0.12 g of 4-methoxyphenol as a polymerization inhibitor
  7. distillationdistilled under a vacuum
  8. concentrationto be concentrated
  9. customwhile removing toluene
  10. customto obtain a lightly yellowish, transparent liquid as the crude product
  11. customwas purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate mixture)

Sources & evidence

ORD record
ord-eb84d18e5ed849de984126fa9d00dba7
Source dataset
uspto-grants-2004_12
Patent number
US06835844B2

Reaction notes

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