Methanesulfonic Acid → HCID 178481674, compound

HRID 32300Notes

Reaction equation

HRID 32300 reaction equation
O=[C:2]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)[CH2:3][C:4](OCC)=[O:5].[CH3:15][NH:16][C:17]([NH2:19])=[S:18].C1CCN2C(=NCCC2)CC1.CS(O)(=O)=O>O>[SH:18][C:17]1[N:16]([CH3:15])[C:4](=[O:5])[CH:3]=[C:2]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:19]=1

Participants

6

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 72.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ethyl 3-oxo-3-(4-pyridyl)propionate (29.0 g, 150 mmol), N-methyl thiourea (40.6 g, 450 mmol) and 1,8-diazabicyclo[5,4,0]-7-undecene (22.4 ml, 150 mmol) was refluxed for 4 hours and the solution of methanesulfonic acid (14.4 g, 150 mmol) in water (50 ml) was added after cooling by ice-water. The precipitate was washed with water, filtered and dried to give the title compound (23.7 g, 72%).

Workup

  1. washThe precipitate was washed with water
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-a981887976cc402f91b7d994d17d8f60
Source dataset
uspto-grants-2008_09
Patent number
US07427615B2

Reaction notes

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