Water → HCID 58231724, compound

HRID 408073Notes

Reaction equation

HRID 408073 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[C:4]([C:14]2[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:31])[CH:29]=[CH2:30].O>C(Cl)Cl>[C:28]([O:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:4]2[C:5]3[S:6][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=3[CH:1]=[CH:2][CH:3]=2)[CH:15]=1)(=[O:31])[CH:29]=[CH2:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 67087638HCID 67087638, compound

Product 1

HCID 58231724HCID 58231724, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.03 g of the thus obtained 3-(4-dibenzothiophenyl)phenol is placed in a round bottom flask and suspended in 15 mL of methylene chloride; after ice cooling the flask, 0.45 g of triethylamine is added; 0.40 g of acryloyl chloride is then added dropwise; after adding the whole, the temperature is returned to room temperature; and the mixture is stirred for 30 minutes. 10 mL of water is added; the mixture is vigorously stirred; an aqueous layer is then removed; the aqueous layer is washed with methylene chloride and ethyl acetate, respectively and then gathered with the original methylene chloride solution; and the mixture is dried upon application of magnesium sulfate. The resulting mixture is concentrated by filtration with a filter paper; and the concentrate is separated by a silica gel column (eluate: hexane/ethyl acetate=80/20 (volume ratio)) to concentrate a component having an Rf of 0.50, thereby obtaining 0.90 g (yield: 73%) of the foregoing white solid. 1H NMR (CDCl3, 400 MHz): δ (ppm) 6.03 (dd=1.2 & 10.4 Hz, 1H), 6.36 (dd=10.4 & 17.2 Hz, 1H), 6.64 (dd=1.2 &17.2 Hz, 1H), 7.20 to 7.24 (m, 1H), 7.44 to 7.55 (m, 6H), 7.62 to 7.65 (m, 1H), 7.82 to 7.85 (m, 1H), 8.14 to 8.19 (m, 2H)

Workup

  1. additionafter adding the whole
  2. customis returned to room temperature
  3. stirringthe mixture is vigorously stirred
  4. customan aqueous layer is then removed
  5. washthe aqueous layer is washed with methylene chloride and ethyl acetate
  6. dry with materialand the mixture is dried upon application of magnesium sulfate
  7. concentrationThe resulting mixture is concentrated by filtration with a filter paper
  8. customand the concentrate is separated by a silica gel column (eluate: hexane/ethyl acetate=80/20 (volume ratio))
  9. concentrationto concentrate a component

Sources & evidence

ORD record
ord-7fba5923359749809704e9b5285d0339
Source dataset
uspto-grants-2014_06
Patent number
US08758960B2

Reaction notes

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