Dichloromethane → HCID 58231717, compound

HRID 408074Notes

Reaction equation

HRID 408074 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:19]=[C:18]([C:20]3[C:25]4[S:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:24]=4[CH:23]=[CH:22][CH:21]=3)[CH:17]=[CH:16][C:15]=2[OH:33])=[CH:3][CH:2]=1.C(Cl)Cl.C(N(CC)CC)C.[C:44](Cl)(=[O:47])[CH:45]=[CH2:46]>O>[C:44]([O:33][C:15]1[CH:16]=[CH:17][C:18]([C:20]2[C:25]3[S:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:24]=3[CH:23]=[CH:22][CH:21]=2)=[CH:19][C:14]=1[C:4]1[C:5]2[S:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[C:9]=2[CH:1]=[CH:2][CH:3]=1)(=[O:47])[CH:45]=[CH2:46]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 67087349HCID 67087349, compound

Product 1

HCID 58231717HCID 58231717, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.02 g of the thus obtained 2,4-bis(4-dibenzothiophenyl)phenol is placed in a round bottom flask; 5 mL of methylene chloride is added to form a transparent solution; after ice cooling the flask, 0.27 g of triethylamine is added; 0.24 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 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 0.42, thereby obtaining 1.0 g (yield: 88%) of the foregoing white solid. 1H NMR (CDCl3, 400 MHz): δ (ppm) 6.05 (dd=1.2 & 10.4 Hz, 1H), 6.37 (dd=10.4 & 17.2 Hz, 1H), 6.66 (dd=1.2 & 17.2 Hz, 1H), 7.30 to 8.25 (m, 17H)

Workup

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

Sources & evidence

ORD record
ord-9abc8d44cfd746f9827c6709dc7e0d22
Source dataset
uspto-grants-2014_06
Patent number
US08758960B2

Reaction notes

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