Carbon Dioxide → HCID 54143672, compound

HRID 1165471Notes

Reaction equation

HRID 1165471 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:18]=[CH:17][C:16]([C:19]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=2)=[CH:20][C:21](O)=[O:22])=[CH:15][CH:14]=1.C(=O)=O.[NH:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1>O1CCCC1>[C:13]1([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:14]=[CH:15][C:16]([C:19]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=2)=[CH:20][C:21]([N:43]2[CH2:48][CH2:47][O:46][CH2:45][CH2:44]2)=[O:22])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 53942238HCID 53942238, compound

Product 1

HCID 54143672HCID 54143672, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.7 g of carbonyldiimidazole were added in portions to a solution of 9.4 g of 3-(biphenyl-4-yl)-3-(3,4-dimethoxyphenyl)acrylic acid in 50 ml of anhydrous tetrahydrofuran. After the evolution of CO2 had subsided, 2.5 g of morpholine were added, and the mixture was boiled for 1 hour. After evaporation, the residue was taken up in toluene/water, and the aqueous phase was discarded. The organic phase was washed once more with water, then dried and evaporated. The crude title compound was isolated with a yield of 10.5 g. The crude product was purified on silica gel with toluene/ acetone (9:1). 6.2 g of the title compound were obtained in the form of a yellow resin, Rf: 0.56 ]l (silica gel, toluene/ acetone 7:3).

Workup

  1. customAfter evaporation
  2. washThe organic phase was washed once more with water
  3. customdried
  4. customevaporated
  5. customThe crude title compound was isolated with a yield of 10.5 g
  6. customThe crude product was purified on silica gel with toluene/ acetone (9:1)

Sources & evidence

ORD record
ord-f0541a014bb44681b1c697587eafeb8d
Source dataset
uspto-grants-1990_03
Patent number
US04910200

Reaction notes

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