Benzoyl chloride → HCID 68814475, compound

HRID 732550Notes

Reaction equation

HRID 732550 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.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>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:31](=[O:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 68815098HCID 68815098, compound

Product 1

HCID 68814475HCID 68814475, compoundYield 66%

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 (480 mg, 0.8 mmol), benzoyl chloride (117 mg), tris(dibenzylideneacetone)dipalladium (0) (19.3 mg) and 2-(di-tert-butylphosphino)biphenyl (34.5 mg) in chloroform (8 mL) in a previously degassed sealed vessel. Flush the mixture with nitrogen and heat the sealed mixture overnight at 60° C. Cool the reaction to room temperature and filter though a filtering agent. Concentrate the filtrate and purify (silica gel chromatography, eluting with 0:100 to 30:70 ethyl acetate:hexanes) to give the title compound (66%).

Workup

  1. customa previously degassed
  2. customsealed vessel
  3. customFlush the mixture with nitrogen
  4. temperatureCool
  5. customthe reaction to room temperature
  6. filtrationfilter though a filtering agent
  7. concentrationConcentrate the filtrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 0:100 to 30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-7a47957339c9494f908ec0db4f1cc47a
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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