Tetrahydrofuran → 4'-(N,N-bis(4-methylphenyl)amino)stilbene-2-yl acrylate

HRID 2264120Notes

Reaction equation

HRID 2264120 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1.[O:31]1C[CH2:34][CH2:33][CH2:32]1.C(=O)([O-])O.[Na+].C(Cl)(=O)C=C>O>[C:32]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(=[O:31])[CH:33]=[CH2:34]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 13140Acryloyl chlorideHCID 516892Sodium BicarbonateHCID 666592702-(2-{4-[Bis(4-methylphenyl)amino]phenyl}ethenyl)phenol

Product 1

HCID 575966504'-(N,N-bis(4-methylphenyl)amino)stilbene-2-yl acrylateYield 79.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At first, 14.9 g of the 2-hydroxy-4′-(N,N-bis(4-methylphenyl)amino)stilbene, 100 ml of tetrahydrofuran and 21.5 g of a 12% sodium hydrogen carbonate solution were put in a reaction vessel having a stirrer, a thermometer and a dropping funnel. Under a nitrogen gas flow, 5.17 g of acrylic acid chloride was dropped therein over 30 min at 5° C., and the reaction was further performed for 3 hours at the same temperature. The reaction liquid was put in water, and the mixture was subjected to extraction with toluene, condensation and column-refinement with a silica gel to prepare a crude product. The crude product was then recrystallized with ethanol. Thus, 13.5 g of a yellow needle-form crystal 4′-(N,N-bis(4-methylphenyl)amino)stilbene-2-yl acrylate (compound No. 105 listed before) having a boiling point of 104.1 to 105.2° C. was prepared at a yield of 79.8%.

Workup

  1. waitthe reaction was further performed for 3 hours at the same temperature
  2. customThe reaction liquid
  3. extractionthe mixture was subjected to extraction with toluene, condensation and column-refinement with a silica gel
  4. customto prepare a crude product
  5. customThe crude product was then recrystallized with ethanol
  6. customwas prepared at a yield of 79.8%

Sources & evidence

ORD record
ord-1fde1cf748e144e8bda90dbd2ad134d7
Source dataset
uspto-grants-2010_12
Patent number
US07855040B2

Reaction notes

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