Phenacyl bromide → HCID 23143315, compound

HRID 732207Notes

Reaction equation

HRID 732207 reaction equation
[CH2:1]([N:3]([CH2:11][CH3:12])[CH2:4][CH2:5][CH2:6][NH:7][C:8]([NH2:10])=[S:9])[CH3:2].Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O.[H-].[Na+].Cl[CH2:26][C:27]1[CH:46]=[CH:45][C:30]([CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][C:41]([O:43]C)=[O:42])=[CH:35][CH:34]=2)=[CH:29][CH:28]=1.P([O-])(O)(O)=O.[K+].[OH-].[Na+]>C(O)C.CN(C)C=O>[CH2:11]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][N:7]([CH2:26][C:27]1[CH:46]=[CH:45][C:30]([CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][C:41]([OH:43])=[O:42])=[CH:35][CH:34]=2)=[CH:29][CH:28]=1)[C:8]1[S:9][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:10]=1)[CH3:12]

Participants

9

Reactant 6

HCID 6259Phenacyl bromideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 516951Monobasic potassium phosphate2×HCID 3034968Pseudourea, 3-(diethylaminopropyl)-2-thio-HCID 23082857Methyl 3-(4-([4-(chloromethyl)benzyl]oxy)phenyl)propanoate

Product 1

HCID 23143315HCID 23143315, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-[3-(diethylamino)propyl]thiourea (90 mg), 2-bromo-1-phenylethanone (100 mg) and N,N-dimethylformamide (3 mL) was stirred at room temperature for 1 hr. Sodium hydride (60% in oil, 40 mg) was added to the mixture under ice-cooling. The mixture was allowed to warm to room temperature and stirred for 1 hr. Methyl 3-(4-{[4-(chloromethyl)benzyl]-oxy}phenyl)propanoate (159 mg) was added to the reaction mixture under ice-cooling, allowed to warm to room temperature and stirred for 1 hr. The reaction mixture was poured into aqueous potassium dihydrogenphosphate solution and the mixture was extracted with ethyl acetate. The ethyl acetate layer was concentrated and the residue was purified by basic silica gel column chromatography to give a yellow oil. A mixture of the yellow oil, 2N aqueous sodium hydroxide solution (2 mL) and ethanol (5 mL) was stirred at room temperature for 1 hr. The reaction mixture was poured into aqueous potassium dihydrogenphosphate solution, and extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.) and concentrated to give the title compound (142 mg, yield 51%) as a yellow oil.

Workup

  1. temperaturecooling
  2. temperatureto warm to room temperature
  3. stirringstirred for 1 hr
  4. temperaturecooling
  5. temperatureto warm to room temperature
  6. stirringstirred for 1 hr
  7. extractionthe mixture was extracted with ethyl acetate
  8. concentrationThe ethyl acetate layer was concentrated
  9. customthe residue was purified by basic silica gel column chromatography
  10. customto give a yellow oil
  11. stirringwas stirred at room temperature for 1 hr
  12. extractionextracted with ethyl acetate
  13. dry with materialThe ethyl acetate layer was dried
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-b2e362e7969f42948b9579cc03a9c2c8
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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