Methanesulfonic Acid → HCID 178481674, compound

HRID 271311Notes

Reaction equation

HRID 271311 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=O)[CH2:8][C:9]([O:11]CC)=O)=[CH:3][CH:2]=1.[CH3:15][NH:16][C:17]([NH2:19])=[S:18].N12CCCN=C1CCCCC2.CS(O)(=O)=O>C(O)C.O>[SH:18][C:17]1[N:16]([CH3:15])[C:9](=[O:11])[CH:8]=[C:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[N:19]=1

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2723704MethylthioureaHCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionate

Product 1

HCID 178481674HCID 178481674, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture containing 70.0 g (0.36 mol) of ethyl 3-(4-pyridinyl)-3-oxopropionate, 98.1 g (1.09 mol) of N-methylthiourea, 55.0 g (0.36 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene in 551 ml of ethanol is heated under reflux during 2 h. The cooled mixture is treated with 34.9 ml (0.36 mol) of methanesulfonic acid in 143.6 ml of water and the precipitate recovered by filtration to afford 60.4 g of pure product as a white solid.

Workup

  1. temperatureis heated
  2. temperatureunder reflux during 2 h
  3. filtrationthe precipitate recovered by filtration

Sources & evidence

ORD record
ord-d8739052d4844a308ccfd460b21d4b05
Source dataset
uspto-grants-2008_11
Patent number
US07452897B2

Reaction notes

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