Ethyl 3-chloro-3-oxopropionate → HCID 67230145, compound

HRID 1511914Notes

Reaction equation

HRID 1511914 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]([Cl:12])=[C:8]([Cl:11])[C:9]=1[Cl:10])=[O:4].[CH2:21]([O:23][C:24](=[O:29])[CH2:25][C:26](Cl)=[O:27])[CH3:22]>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:26](=[O:27])[CH2:25][C:24]([O:23][CH2:21][CH3:22])=[O:29])[C:7]([Cl:12])=[C:8]([Cl:11])[C:9]=1[Cl:10])=[O:4]

Participants

4

Reactant 2

HCID 118931Ethyl 3-chloro-3-oxopropionateHCID 67231047HCID 67231047, compound

Product 1

HCID 67230145HCID 67230145, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-benzylamino-3,4,5-trichloro-1H-pyrrole-2-carboxylic acid methyl ester (394 mg, 1.18 mmol) and chlorocarbonyl-acetic acid ethyl ester (227 μL, 1.77 mmol) in dioxane (5 mL) was stirred under reflux for 30 min; then the reaction mixture was cooled and the solvents were removed, the residue was directly silica gel column purified to give the desired product (278 mg) as colorless syrup. ESI (m/z): 447 (M+H)+.

Workup

  1. temperatureunder reflux for 30 min
  2. temperaturethen the reaction mixture was cooled
  3. customthe solvents were removed
  4. custompurified

Sources & evidence

ORD record
ord-892bdb100f0648ba9b7ea375ece4ecab
Source dataset
uspto-grants-2012_07
Patent number
US08217043B2

Reaction notes

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