Ethyl Acetate → HCID 54525778, compound

HRID 1838492Notes

Reaction equation

HRID 1838492 reaction equation
[OH:1][CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:21])[C:12]([CH3:20])([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH3:13])=[CH:7][CH:6]=1.[CH2:22]([S:26][CH2:27][C:28](=[CH2:32])[C:29](O)=[O:30])[CH2:23][CH2:24][CH3:25].Cl.C(N=C=NCCCN(C)C)C.C(OCC)(=O)C>CC(N(C)C)=O>[CH3:20][C:12]([N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)([CH3:13])[C:11]([C:8]1[CH:9]=[CH:10][C:5]([S:4][CH2:3][CH2:2][O:1][C:29](=[O:30])[C:28]([CH2:27][S:26][CH2:22][CH2:23][CH2:24][CH3:25])=[CH2:32])=[CH:6][CH:7]=1)=[O:21]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18755061HCID 18755061, compoundHCID 18755078HCID 18755078, compound

Product 1

HCID 54525778HCID 54525778, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
-20 °C

Procedure

1.0 g (3.2 mmol) of 1-[4-(2-Hydroxyethylthio)phenyl]-2-methyl-2-morpholin-4-yl-propane-1-one and 0.56 g (3.2 mmol) of 2-(butylthiomethyl)acrylic acid are dissolved in 20 ml of dry dimethylacetamide and cooled to −20° C. To the solution is added 0.68 g (3.54 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride in 5 ml of dry dimethylacetamide. The mixture is gradually warmed to room temperature and stirred overnight. To the mixture is added ethyl acetate. The mixture then is washed with saturated sodium chloride solution and dried over MgSO4. After distilling off the ethyl acetate, the residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:2) as an eluent, and an oily product is obtained.

Workup

  1. temperatureThe mixture is gradually warmed to room temperature
  2. washThe mixture then is washed with saturated sodium chloride solution
  3. dry with materialdried over MgSO4
  4. distillationAfter distilling off the ethyl acetate
  5. customthe residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:2) as an eluent
  6. customan oily product is obtained

Sources & evidence

ORD record
ord-b9dcb442e4a542cb99d2e553eadcc7af
Source dataset
uspto-grants-2004_01
Patent number
US06673850B1

Reaction notes

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