N,N'-Dimethylethylenediamine → 4-(3-(Benzylthio)-2-ethylphenyl)morpholin-3-one

HRID 389643Notes

Reaction equation

HRID 389643 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[C:10]=1[CH2:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][C:19]1=[O:24].CNCCNC.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[CH2:1]([S:8][C:9]1[C:10]([CH2:16][CH3:17])=[C:11]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][C:19]2=[O:24])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 669533-MorpholinoneHCID 66911124Benzyl(3-bromo-2-ethylphenyl)sulfane

Product 1

HCID 669111454-(3-(Benzylthio)-2-ethylphenyl)morpholin-3-one

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Intermediate 5 (1.075 g, 3.5 mmol), morpholin-3-one (389 mg, 3.85 mmol), CuI (67 mg, 0.35 mmol), N,N′-dimethylethylene diamine (75 μl, 0.7 mmol) and K2CO3 (1,064 g, 7.7 mmol) were suspended in toluene (30 ml) under argon and heated to 110° C. for 20 h. After cooling to RT the reaction mixture was quenched by addition of 100 ml sat. aq NH4Cl, 150 ml conc. NH3 in water and 100 ml water and extracted three times with ethyl acetate. The organic layers were combined and washed with water and sat. aq NaCl-solution, dried with MgSO4, filtered and evaporated to dryness. The resulting oil crystallizes upon standing and was triturated with n-heptane-MTBE (19:1).

Workup

  1. temperatureAfter cooling to RT the reaction mixture
  2. customwas quenched by addition of 100 ml sat. aq NH4Cl, 150 ml conc. NH3 in water and 100 ml water
  3. extractionextracted three times with ethyl acetate
  4. washwashed with water and sat. aq NaCl-solution
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe resulting oil crystallizes
  9. customwas triturated with n-heptane-MTBE (19:1)

Sources & evidence

ORD record
ord-deda761df88a490caae9c4ce8dcd535d
Source dataset
uspto-grants-2013_02
Patent number
US08378092B2

Reaction notes

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