HCID 53693524, compound → HCID 19351070, compound

HRID 263422Notes

Reaction equation

HRID 263422 reaction equation
C(O[C:4](=[O:15])[CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:6]([O-:8])=O)C.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH2:26][CH2:27][NH-:28])[CH:21]=[CH:22][C:23]=1[O:24][CH3:25].[CH3:29][O:30][C:31]1[C:36]([O:37][CH3:38])=[C:35]([O:39][CH3:40])[CH:34]=[CH:33][C:32]=1[CH2:41][CH2:42][NH:43][CH2:44][CH2:45][C:46]1[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[C:48]([O:54][CH3:55])[C:47]=1[O:56][CH3:57]>CN(C)C=O>[CH3:57][O:56][C:47]1[C:48]([O:54][CH3:55])=[C:49]([O:52][CH3:53])[CH:50]=[CH:51][C:46]=1[CH2:45][CH2:44][N:43]([CH2:42][CH2:41][C:32]1[CH:33]=[CH:34][C:35]([O:39][CH3:40])=[C:36]([O:37][CH3:38])[C:31]=1[O:30][CH3:29])[C:6](=[O:8])[CH:5]([C:4]([NH:28][CH2:27][CH2:26][C:20]1[CH:21]=[CH:22][C:23]([O:24][CH3:25])=[C:18]([O:17][CH3:16])[CH:19]=1)=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 53693524HCID 53693524, compoundHCID 86738314HCID 86738314, compound

Product 1

HCID 19351070HCID 19351070, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 18.0 g (52.4 mmol) of monoethylphenylmalonate-2-(3,4-dimethoxyphenyl)ethylamide in 150 ml of anhydrous dimethylformamide are added, at ambient temperature 9.0 g (55.5 mmol) of N,N'-carbonyldiimidazole in batches. After 30 minutes 18.0 g (44.3 mmol) of di-[2-(2,3,4-trimethoxyphenyl)ethyl]amine are added and the mixture is stirred for 30 minutes. Then the solvent is distilled off in vacuo, the residue is taken up in 1.5 liters of CH2Cl2 and extracted twice with 250 ml of water and 200 ml of 1N HCl, one after the other. The organic phase is evaporated down after drying over Na2SO4 and, after purification over a silica gel column (eluant: CH2Cl2 /MeOH 100:2) the residue is crystallised from ethyl acetate/ether. Yield: 35.5 g

Workup

  1. distillationThen the solvent is distilled off in vacuo
  2. extractionextracted twice with 250 ml of water and 200 ml of 1N HCl, one after the other
  3. customThe organic phase is evaporated down
  4. dry with materialafter drying over Na2SO4
  5. customafter purification over a silica gel column (eluant: CH2Cl2 /MeOH 100:2) the residue
  6. customis crystallised from ethyl acetate/ether

Sources & evidence

ORD record
ord-93d9f42304ca49629ef71fe3e2659b2b
Source dataset
uspto-grants-1997_07
Patent number
US05643919

Reaction notes

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