Diethyl (ethoxymethylene)malonate → HCID 21192540, compound

HRID 1068043Notes

Reaction equation

HRID 1068043 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH:15]3[CH2:20][CH2:19][S:18][CH2:17][CH2:16]3)=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O[CH:24]=[C:25]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:26]([O:28][CH2:29][CH3:30])=[O:27])C>N1C=CC=CC=1>[N:1]1([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([N:14]([CH:24]=[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:15]3[CH2:20][CH2:19][S:18][CH2:17][CH2:16]3)=[CH:12][CH:13]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonate2×HCID 21192595HCID 21192595, compound

Product 1

HCID 21192540HCID 21192540, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
160 °C

Procedure

A flask containing N-[4-(4-morpholinylmethyl)phenyl]tetrahydro-2H-thiopyran-4-amine (0.44 g) is treated with diethyl ethoxymethylenemalonate (0.35 mL). The flask is tightly capped and heated to 160° C. for 2 hours. The reaction is cooled to room temperature, treated with diethyl ethoxymethylenemalonate (0.35 mL) and pyridine (0.35 mL) and heated to 150° C. for 1 hour in a tightly sealed flask. The reaction is cooled to room temperature and azeotroped under reduced pressure with toluene (3×). The residue is flash column chromatographed on silica gel eluting with ethyl acetate. The product-containing fractions are evaporated to give 0.59 g of diethyl 2-{[4-(4-morpholinylmethyl)(tetrahydro-2H-thiopyran-4-yl)anilino]methylene}malonate as a tan solid.

Workup

  1. customThe flask is tightly capped
  2. temperatureThe reaction is cooled to room temperature
  3. temperatureheated to 150° C. for 1 hour in a tightly sealed flask
  4. temperatureThe reaction is cooled to room temperature
  5. customazeotroped under reduced pressure with toluene (3×)
  6. customchromatographed on silica gel eluting with ethyl acetate
  7. customThe product-containing fractions are evaporated

Sources & evidence

ORD record
ord-8ad8119a0086469ca089ea691ba3c3d9
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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