Sodium Carbonate → HCID 17874606, compound

HRID 2299313Notes

Reaction equation

HRID 2299313 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5](=[CH:11][N:12]([CH3:25])[C:13]1[S:14][CH:15]=[CH:16][C:17]=1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[Cl-].[CH2:28]=[N+:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH2:9]([O:8][C:6](=[O:7])[C:5](=[CH:11][N:12]([CH3:25])[C:13]1[S:14][C:15]([CH2:28][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[CH:16][C:17]=1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:4]([O:3][CH2:1][CH3:2])=[O:26])[CH3:10]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11367014Morpholinium, 4-methylene-, chlorideHCID 17874593HCID 17874593, compound

Product 1

HCID 17874606HCID 17874606, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(3-tert-butoxycarbonyl-thien-2-yl)-methylaminomethylene-malonic acid diethyl ester (19.0 g) from Preparation No. 2 and 4-methylene morpholinium chloride (Dimmock, JR, et al Eur. J. Med. Chem. 1989, 24, 379-383) (13.4 g) in dry acetonitrile (50 ml) is heated at reflux for about 4 hr. The solution is then cooled in an ice bath and saturated aqueous sodium carbonate (98 ml) is slowly added. The solution is extracted three times with ethyl acetate (300 ml total) and the combined organic layers are then washed three times with water (600 ml total). The solvents are removed in vacuo to afford 23.0 g (96%) of the title compound as a brown oil.

Workup

  1. customfrom Preparation No
  2. temperatureat reflux for about 4 hr
  3. temperatureThe solution is then cooled in an ice bath
  4. extractionThe solution is extracted three times with ethyl acetate (300 ml total)
  5. washthe combined organic layers are then washed three times with water (600 ml total)
  6. customThe solvents are removed in vacuo

Sources & evidence

ORD record
ord-1188e48f34e443d6b0c32cb769a25a7d
Source dataset
uspto-grants-2002_12
Patent number
US06495683B2

Reaction notes

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