Potassium Carbonate → HCID 18321654, compound

HRID 1249706Notes

Reaction equation

HRID 1249706 reaction equation
[C:1]([C:3]1[CH:24]=[CH:23][C:6]([NH:7][CH2:8][CH2:9][N:10]([CH2:17][C:18]([O:20]CC)=[O:19])[CH2:11][C:12](OCC)=[O:13])=[CH:5][CH:4]=1)#[N:2].C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[K+].[K+].O.[OH-].[Li+]>C(#N)C.CO.O>[C:1]([C:3]1[CH:24]=[CH:23][C:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:17][C:18]([OH:20])=[O:19])[CH2:11][C:12]2=[O:13])=[CH:5][CH:4]=1)#[N:2]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 168937Lithium hydroxide, monohydrateHCID 18321692HCID 18321692, compound

Product 1

HCID 18321654HCID 18321654, compoundYield 60.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A suspension of ethyl 2-[2-(4-cyanoanilino)ethyl(2-ethoxy-2-oxoethyl)amino]acetate (58 g, 0.174 mol), diisopropylethylamine (4 g, 0.03 mol) and potassium carbonate (24 g, 0.174 mol) in 400 ml of acetonitrile is refluxed for 2 days. The mixture is filtered and rinsed with dichloromethane. The filtrate is evaporated to give a brown solid, which is dissolved in 150 ml of methanol and 50 ml of water, followed by addition of lithium hydroxide monohydrate (8.4 g, 0.2 mol). After stirring for 30 minutes at room temperature, half of the methanol is removed under vacuum to give a suspension. About 100 ml of water are added and the mixture is acidified at 5° C. The product is filtered off, rinsed with water and dried under vacuum at 50° C. to give 27.2 g of a beige-coloured powder.

Workup

  1. temperatureis refluxed for 2 days
  2. filtrationThe mixture is filtered
  3. washrinsed with dichloromethane
  4. customThe filtrate is evaporated
  5. customto give a brown solid, which
  6. customhalf of the methanol is removed under vacuum
  7. customto give a suspension
  8. customis acidified at 5° C
  9. filtrationThe product is filtered off
  10. washrinsed with water
  11. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-d9067174063a4a089a919cfa69e768d6
Source dataset
uspto-grants-2002_01
Patent number
US06335337B1

Reaction notes

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