Potassium Carbonate → HCID 178437199, compound

HRID 706093Notes

Reaction equation

HRID 706093 reaction equation
[C:1](=[NH:21])([O:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([CH3:20])[CH:14]=2)=[CH:8][CH:7]=1)[NH2:2].[CH2:22](/[C:24](=[CH:30]/O)/[C:25](OCC)=[O:26])[CH3:23].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:9]2[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][O:3][C:1]3[NH:2][CH:30]=[C:24]([CH2:22][CH3:23])[C:25](=[O:26])[N:21]=3)=[CH:11][CH:10]=2)=[CH:14][C:15]=1[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21058694ethyl(2Z)-2-ethyl-3-hydroxy-2-propenoateHCID 677759512-{4-[(4-Chloro-3-methylphenyl)oxy]phenyl}ethyl imidocarbamate

Product 1

HCID 178437199HCID 178437199, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-{4-[(4-chloro-3-methylphenyl)oxy]phenyl}ethyl imidocarbamate (130 mg, 0.427 mmol), ethyl (2Z)-2-ethyl-3-hydroxy-2-propenoate (123 mg, 0.853 mmol) and K2CO3 (118 mg, 0.853 mmol) in DMF (3 mL) was heated with a microwave condition at 110° C. for 1.5 h. After cooling, the mixture was filtered, and purified via MDAP to afford the title compound (50 mg, 30.5% yield) as white solid. LCMS: rt=3.80 min, [M+H+]=385

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. custompurified via MDAP

Sources & evidence

ORD record
ord-70a9c1ce78374e15bd88757147f87cc1
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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