Water → HCID 66869728, compound

HRID 241421Notes

Reaction equation

HRID 241421 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:18])[CH2:13][O:14][CH2:15][CH2:16]Cl)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[Cs+].[Cs+].O>C(#N)C>[NH2:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][C:12]2=[O:18])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 10796Cesium carbonateHCID 67495107HCID 67495107, compound

Product 1

HCID 66869728HCID 66869728, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

22.2 5.2 g (0.016 mol) of N-(3-amino-4-nitrophenyl)-2-(2-chloroethoxy)acetamide are suspended in 250 ml of acetonitrile, and 6.6 g (0.02 mol) of caesium carbonate are added. The mixture is stirred at room temperature for 18 h. The batch is poured into about 250 ml of water and extracted 3× with 200 ml of ethyl acetate each time. The entire organic phases are dried using anhydrous sodium sulfate, filtered, and the solvent is stripped off in a Rotavapor to a residual volume of about 150 ml. The crystals deposited during evaporation in the rotary evaporator are separated off and dried, giving 4-(3-amino-4-nitrophenyl)morpholin-3-one, HPLC-MS [M+H]+ 238.1.

Workup

  1. extractionextracted 3× with 200 ml of ethyl acetate each time
  2. customThe entire organic phases are dried
  3. filtrationfiltered
  4. customThe crystals deposited during evaporation in the rotary evaporator
  5. customare separated off
  6. customdried

Sources & evidence

ORD record
ord-cc08604804424da8a00ab59249964835
Source dataset
uspto-grants-2014_02
Patent number
US08648201B2

Reaction notes

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