2-Chloroethanol → HCID 22033500, compound

HRID 325047Notes

Reaction equation

HRID 325047 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-d36de05eb0cd4d1eb6421693e8c0bb47
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

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