Cesium carbonate → HCID 17982603, compound

HRID 2246812Notes

Reaction equation

HRID 2246812 reaction equation
Cl[C:2]1(Cl)[CH2:7][O:6][CH2:5][CH2:4][O:3]1.[CH3:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[NH2:13].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:9][C:10]1[CH:11]=[C:12]([N:13]2[CH2:2][CH2:7][O:6][CH2:5][C:4]2=[O:3])[CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 118984-Nitro-m-toluidineHCID 124243252,2-Dichloro-1,4-dioxane

Product 1

HCID 17982603HCID 17982603, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

12.8 g of 2-chlorodioxene (contains 6% of 2,2-dichlorodioxane) are added to a solution of 10.0 g (65.7 mmol) of 3-methyl-4-nitroaniline in 250 ml of acetonitrile, and the mixture is stirred at 80° C. for 66 hours. The reaction solution is cooled to room temperature, 42.8 g (131 mmol) of caesium carbonate are added, and the mixture is stirred at room temperature for 18 hours. The reaction mixture is filtered, the residue is washed well with acetonitrile, and the filtrate is evaporated. The residue is recrystallised from a little acetonitrile, giving 12.8 g (83%) of 4-(3-methyl-4-nitrophenyl)morpholin-3-one as yellowish solid. ESI 236. 1H-NMR (d6-DMSO): δ=2.54 (s; 2H), δ=3.82 (t, J=5 Hz; 2H), 4.00 (t, J=5 Hz; 2H), 4.25 (s; 2H), 7.57 (m; 2H), 8.04 (d, J.=8 Hz; 1H).

Workup

  1. temperatureThe reaction solution is cooled to room temperature
  2. stirringthe mixture is stirred at room temperature for 18 hours
  3. filtrationThe reaction mixture is filtered
  4. washthe residue is washed well with acetonitrile
  5. customthe filtrate is evaporated
  6. customThe residue is recrystallised from a little acetonitrile

Sources & evidence

ORD record
ord-d29b382c5c3747a3a76a86025298e682
Source dataset
uspto-grants-2010_03
Patent number
US07687624B2

Reaction notes

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