Phenacyl bromide → HCID 23143333, compound

HRID 732206Notes

Reaction equation

HRID 732206 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]([NH2:13])=[S:12])=[CH:4][CH:3]=1.Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O.[H-].[Na+].Cl[CH2:27][C:28]1[CH:47]=[CH:46][C:31]([CH2:32][O:33][C:34]2[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][C:42]([O:44]C)=[O:43])=[CH:36][CH:35]=2)=[CH:30][CH:29]=1.P([O-])(O)(O)=O.[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]([CH2:27][C:28]2[CH:47]=[CH:46][C:31]([CH2:32][O:33][C:34]3[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][C:42]([OH:44])=[O:43])=[CH:36][CH:35]=3)=[CH:30][CH:29]=2)[C:11]2[S:12][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:13]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 6259Phenacyl bromideHCID 24758Sodium hydrideHCID 516951Monobasic potassium phosphateHCID 12398786N-[2-(4-Chlorophenyl)ethyl]thioureaHCID 23082857Methyl 3-(4-([4-(chloromethyl)benzyl]oxy)phenyl)propanoate

Product 1

HCID 23143333HCID 23143333, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-[2-(4-chlorophenyl)ethyl]thiourea (108 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 this mixture under ice-cooling, 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, and the mixture was allowed to warm to room temperature and further 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 preparative HPLC (gradient cycle A) to give the title compound (113 mg, yield 39%) 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. stirringfurther stirred for 1 hr
  7. extractionthe mixture was extracted with ethyl acetate
  8. concentrationThe ethyl acetate layer was concentrated
  9. customthe residue was purified by preparative HPLC (gradient cycle A)

Sources & evidence

ORD record
ord-a16160297f82463b96bd4c6c5f88b6ed
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

Loading…