Carbon Dioxide → HCID 53791687, compound

HRID 580615Notes

Reaction equation

HRID 580615 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)=[C:11]([CH3:16])[CH2:12][C:13]([OH:15])=O)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.C(=O)=O.[NH:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][C:10]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)=[C:11]([CH3:16])[CH2:12][C:13]([N:42]2[CH2:47][CH2:46][O:45][CH2:44][CH2:43]2)=[O:15])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 53654367HCID 53654367, compound

Product 1

HCID 53791687HCID 53791687, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.38 g (15 mmols) of 5-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-2-methyl-penta-2,4-diene-1-carboxylic acid were dissolved in 30 ml of absolute tetrahydrofuran, and 3.24 g (20 mmols) of 1,1'-carbonyldiimidazole were added in portions thereto. After the evolution of CO2 had ended, 1.74 (20 mmols) of morpholine were added, the mixture was allowed to stand at room temperature for 10 minutes and was then refluxed for 2 hours. The solution was evaporated in vacuo, and the residue was shaken with toluene/water. The toluene phase was again washed with water, then dried and concentrated down to about 20 ml in vacuo. This solution was purified on a chromatography column charged with 30 g of silica gel mixed with toluene. Elution was carried out first with toluene and then with a toluene-acetone mixture (90:10). The fractions containing the substance with an Rf 0.52 (toluene/acetone 70:30 on silica gel plate) were collected and evaporated in vacuo.

Workup

  1. temperaturewas then refluxed for 2 hours
  2. customThe solution was evaporated in vacuo
  3. washThe toluene phase was again washed with water
  4. customdried
  5. concentrationconcentrated down to about 20 ml in vacuo
  6. customThis solution was purified on a chromatography column
  7. additioncharged with 30 g of silica gel
  8. additionmixed with toluene
  9. washElution
  10. additionThe fractions containing the substance with an Rf 0.52 (toluene/acetone 70:30 on silica gel plate)
  11. customwere collected
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-ec55d9f18f3c425ebd4e12947c506891
Source dataset
uspto-grants-1988_06
Patent number
US04753934

Reaction notes

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