2-Chloroethanol → HCID 22033500, compound

HRID 1791868Notes

Reaction equation

HRID 1791868 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+].Cl[CH2:35][CH2:36][OH:37].[Na+].[I-]>CN(C=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:13]=[C:14]([N:18]([CH2:35][CH2:36][OH:37])[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:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 22033496HCID 22033496, compound

Product 1

HCID 22033500HCID 22033500, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-{3-[2-(4-cyanophenyl)ethoxy]phenyl}benzenesulfonamide (0.093 g; 0.246 mmol; from Example 1(iv) above), K2CO3 (0.047 g, 0.34 mmol), 2-chloroethanol (0.028 g; 0.34 mmol) and NaI (0.052 g; 0.34 mmol) were stirred in DMF (4 mL) for 24 hours at 100° C. The solvent was removed in vacuo. The residue was dissolved in water and extracted twice with EtOAc. The combined organic portions were washed with brine, dried (Na2SO4) and the solvent evaporated. Purification by flash chromatography (SiO2; toluene:EtOAc 10:0, 9:1, 8:2, 6:4) afforded 0.047 g (45%) of the sub-title compound.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted twice with EtOAc
  4. washThe combined organic portions were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated
  7. customPurification by flash chromatography (SiO2; toluene:EtOAc 10:0, 9:1, 8:2, 6:4)

Sources & evidence

ORD record
ord-a760ed3aa08d43f0a0a97f8b15340fd1
Source dataset
uspto-grants-2006_07
Patent number
US07074820B2

Reaction notes

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