Ethyl bromoacetate → HCID 86584802, compound

HRID 325046Notes

Reaction equation

HRID 325046 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:13]=[C:14]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:15]=[CH:16][CH:17]=2)=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37]>CN(C=O)C>[C:22]1([S:19]([N:18]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:10][CH2:9][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)[CH:13]=2)(=[O:21])=[O:20])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 22033496HCID 22033496, compound

Product 1

HCID 86584802HCID 86584802, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-{3-[2-(4-Cyanophenyl)ethoxy]phenyl}benzenesulfonamide (0.179 g; 0.47 mmol; from Example 1(iv) above), K2CO3 (0.082 g; 0.59 mmol) and ethyl bromoacetate (63 μL; 0.57 mmol) were stirred in DMF (10 mL) for 1 hour at room temperature, then 1 hour at 60° C. The mixture was filtered and the solvent removed in vacuo. The residue was dissolved in EtOAc and washed with water. The aqueous phase was extracted with EtOAc. The combined organic portions were dried (Na2SO4) and the solvent evaporated to afford the sub-title compound in a quantitative yield.

Workup

  1. custom1 hour
  2. customat 60° C
  3. filtrationThe mixture was filtered
  4. customthe solvent removed in vacuo
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with water
  7. extractionThe aqueous phase was extracted with EtOAc
  8. dry with materialThe combined organic portions were dried (Na2SO4)
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-0c64b62a26b34d0ea2021fcbfb055547
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

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