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Ethyl bromoacetate → HCID 86584802, compound

HRID 1791867
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Reaction equation

HRID 1791867 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-8b5caf0ce965422b920c209aacc255dd
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07074820B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes