Tetrahydrofuran → HCID 19734465, compound

HRID 327035Notes

Reaction equation

HRID 327035 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([OH:16])=[O:15])=[C:12]([CH3:17])[NH:11][C:10]([CH3:18])=[C:9]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:5]=[CH:6][CH:7]=1.C(N1C=CN=C1)(N1[CH:30]=[CH:29]N=C1)=O.C1C[O:39]CC1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:9]([C:19]([O:21][CH2:22][CH2:23][OH:39])=[O:20])=[C:10]([CH3:18])[NH:11][C:12]([CH3:17])=[C:13]2[C:14]([O:16][CH2:29][CH3:30])=[O:15])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 4346467148455-50-9

Product 1

HCID 19734465HCID 19734465, compound

Procedure

3.4 g (10 mmol) of 4-(3-chlorophenyl)-3-(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-5-carboxylic acid and 2 g (10 mmol) of carbonyldiimidazole are stirred overnight at room temperature in 50 ml of abs. THF. The mixture is evaporated, the residue is taken up in 50 ml of ethyl acetate and the mixture is washed twice with 50 ml of water each time. After drying over Na2SO4, the solvent is distilled off and the residue (3.55 g) is dissolved in 10 ml of abs. THF. After addition of 100 ml of ethylene glycol and 100 mg of NaH, the mixture is stirred at room temperature for 3 h, mixed with 100 ml of ethyl acetate and extracted twice by shaking with 100 ml of water each time. After drying over sodium sulphate, the extract is evaporated. The residue is homogeneous in the TLC and is further processed directly. Yield: 2.95 g (83% of theory)

Workup

  1. customThe mixture is evaporated
  2. washthe mixture is washed twice with 50 ml of water each time
  3. dry with materialAfter drying over Na2SO4
  4. distillationthe solvent is distilled off
  5. dissolutionthe residue (3.55 g) is dissolved in 10 ml of abs
  6. additionAfter addition of 100 ml of ethylene glycol and 100 mg of NaH
  7. additionmixed with 100 ml of ethyl acetate
  8. extractionextracted twice
  9. stirringby shaking with 100 ml of water each time
  10. dry with materialAfter drying over sodium sulphate
  11. customthe extract is evaporated

Sources & evidence

ORD record
ord-b1176af4ff7943d6b9c5610b124bf197
Source dataset
uspto-grants-1993_12
Patent number
US05272161

Reaction notes

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