Diethyl (ethoxymethylene)malonate → HCID 11317628, compound

HRID 2119328Notes

Reaction equation

HRID 2119328 reaction equation
[CH2:1]([N:8]([CH3:23])[C:9]1[C:10]([NH2:22])=[CH:11][CH:12]=[C:13]([CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[CH:27]=[C:28]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:29]([O:31][CH2:32][CH3:33])=[O:30])C>C(OCC)(=O)C.CCCCCC>[CH2:1]([N:8]([CH3:23])[C:9]1[CH:14]=[C:13]([CH2:15][N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[CH:12]=[CH:11][C:10]=1[NH:22][CH:27]=[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 11312962HCID 11312962, compound

Product 1

HCID 11317628HCID 11317628, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N2-benzyl-N2-methyl-4-(4-morpholinylmethyl)-1,2-benzenediamine (3.1 g, 10 mmol) and diethyl ethoxymethylenemalonate (4.2 g, 20 mmol) is heated at 120° C. until HPLC shows that the reaction is complete (20 min). The product is applied in 10% ethyl acetate/hexane to a silica gel column which is eluted with 20% ethyl acetate/hexane to remove excess diethyl ethoxymethylenemalonate and then with 50% ethyl acetate/hexane to elute 3.7 g of the title compound as an oil.

Workup

  1. custom(20 min)
  2. washis eluted with 20% ethyl acetate/hexane
  3. customto remove excess diethyl ethoxymethylenemalonate
  4. washwith 50% ethyl acetate/hexane to elute 3.7 g of the title compound as an oil

Sources & evidence

ORD record
ord-73942c0b0824479b954e696ff5fcb8e2
Source dataset
uspto-grants-2004_02
Patent number
US06686356B2

Reaction notes

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