Water → HCID 22602178, compound

HRID 2308390Notes

Reaction equation

HRID 2308390 reaction equation
C(N(CC)CC)C.Cl[CH2:9][CH2:10][C:11]([S:13][CH2:14][CH:15]1[CH2:19][S:18][CH:17]([CH2:20][S:21][CH2:22][S:23][CH2:24][CH:25]2[S:29][CH:28]([CH2:30][S:31][C:32](=[O:36])[CH2:33][CH2:34]Cl)[CH2:27][S:26]2)[S:16]1)=[O:12].O.C1(C)C=CC=CC=1>CC(C)=O>[C:11]([S:13][CH2:14][CH:15]1[CH2:19][S:18][CH:17]([CH2:20][S:21][CH2:22][S:23][CH2:24][CH:25]2[S:29][CH:28]([CH2:30][S:31][C:32](=[O:36])[CH:33]=[CH2:34])[CH2:27][S:26]2)[S:16]1)(=[O:12])[CH:10]=[CH2:9]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 8471TriethylamineHCID 22602160HCID 22602160, compound

Product 1

HCID 22602178HCID 22602178, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Next, 40.0 g (0.39 mol) of triethylamine was added dropwise to a solution of 76.7 g of bis[4-(3-chloropropionylthiomethyl)-1,3-dithiolan-2-ylmethyl-thio]methane prepared above, dissolved in 300 g of acetone, at 2 to 5° 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 pure 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 crude product as a lightly yellowish, transparent liquid. The crude product thus prepared was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate mixture), to obtain 51.6 g (0.10 mol) of bis[4-(acryloylthiomethyl)-1,3-dithiolan-2-ylmethylthio]methane, which was a colorless, transparent liquid.

Workup

  1. customprepared above,
  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 pure 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 crude product as a lightly yellowish, transparent liquid
  11. customwas purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate mixture)

Sources & evidence

ORD record
ord-e539979450a247d581615fa9255d5176
Source dataset
uspto-grants-2004_12
Patent number
US06835844B2

Reaction notes

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