Diethyl (ethoxymethylene)malonate → HCID 21192526, compound

HRID 1067957Notes

Reaction equation

HRID 1067957 reaction equation
[CH:1]1([NH:4][C:5]2[CH:10]=[CH:9][C:8]([CH2:11][N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.C(O[CH:21]=[C:22]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24])C>N1C=CC=CC=1>[CH:1]1([N:4]([CH:21]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:5]2[CH:6]=[CH:7][C:8]([CH2:11][N:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)=[CH:9][CH:10]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 21192542HCID 21192542, compound

Product 1

HCID 21192526HCID 21192526, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
145 °C

Procedure

To a flask containing N-cyclopropyl-4-(4-morpholinylmethyl)aniline (0.55 g) from Preparation No. 23 is added diethyl ethoxymethylenemalonate (0.45 mL) and pyridine (0.33 mL). The flask is tightly capped and heated to 145° C. for 2 hours. The reaction is cooled to room temperature and azeotroped under reduced pressure with toluene (3×). The residue is dissolved in dichloromethane and washed with brine, dried and concentrated under reduced pressure. The residue is chromatographed on silica eluting with 2% to 6% methanol in dichloromethane. The product-containing fractions are evaporated to give 0.77 g of the title compound as an oil.

Workup

  1. customfrom Preparation No
  2. customThe flask is tightly capped
  3. temperatureThe reaction is cooled to room temperature
  4. customazeotroped under reduced pressure with toluene (3×)
  5. dissolutionThe residue is dissolved in dichloromethane
  6. washwashed with brine
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is chromatographed on silica eluting with 2% to 6% methanol in dichloromethane
  10. customThe product-containing fractions are evaporated

Sources & evidence

ORD record
ord-068f9a7f45b741cd987ab3ff890bbff2
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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