Methacryloyl chloride → HCID 69020374, compound

HRID 1436698Notes

Reaction equation

HRID 1436698 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:16]=[C:15]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[CH3:31][C:32](=[CH2:36])[C:33](Cl)=[O:34].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C(Cl)(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:16]=[C:15]([C:33](=[O:34])[C:32]([CH3:36])=[CH2:31])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[CH3:13][N:9]([CH2:10][CH2:11][CH3:12])[C:7](=[O:8])[C:6]1[CH:5]=[C:4]([CH:16]=[C:15]([C:33](=[O:34])[C:32]([CH3:36])=[CH2:31])[CH:14]=1)[C:3]([OH:2])=[O:30]

Participants

6

Reactant 3

HCID 13528Methacryloyl chlorideHCID 75806TricyclohexylphosphineHCID 68815098HCID 68815098, compound

Product 1

HCID 69020374HCID 69020374, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Dissolve N-methyl-N-propyl-5-tributylstannanyl-isophthalamic acid methyl ester (885 mg, 168 mmol), 2-methyl-acryloyl chloride (172 mg, 1.64 mmol), tris(dibenzylideneacetone)dipalladium (46 mg, 0.05 mmol) and tricyclohexylphosphine (46 mg, 0.16 mmol)) in chloroform (15.5 mL) in a previously degassed vessel. Flush the mixture with nitrogen gas and heat the sealed mixture overnight at 60° C. Cool to room temperature and filter though a filtering agent. Concentrate the filtrate and purify (silica gel chromatography, eluting with 0:100 to 20:80 ethyl acetate:hexanes) to give the title compound.

Workup

  1. customFlush the mixture with nitrogen gas
  2. temperatureCool to room temperature
  3. filtrationfilter though a filtering agent
  4. concentrationConcentrate the filtrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 0:100 to 20:80 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-57a1421e497c4f91a8a2589158cdb4e3
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

Loading…