Hydrochloric Acid → HCID 22033496, compound

HRID 325026Notes

Reaction equation

HRID 325026 reaction equation
O.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)[CH:4]=1.Cl.[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>N1C=CC=CC=1>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][O:9][C:5]2[CH:4]=[C:3]([NH:2][S:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:29])=[O:28])[CH:8]=[CH:7][CH:6]=2)=[CH:17][CH:16]=1)#[N:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 22033543HCID 22033543, compound

Product 1

HCID 22033496HCID 22033496, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cold (ice:water temperature) solution of amino-3-[2-(4-cyanophenyl)ethoxy]benzene×HCl (231 mg; 0.84 mmol; from step (iii) above) in pyridine (2 mL) was added benzenesulfonyl chloride (119 μL; 0.93 mmol) and the mixture was allowed to reach room temperature and stirred for three days. The pyridine was removed by evaporation and the residue was partitioned between water and EtOAc. The phases was separated and the water phase was extracted twice with EtOAc and the combined organic phase was washed once with 1M KHSO4, brine and dried (Na2SO4). The solvent was evaporated and the residue was subjected to purification by flash chromatography using a stepwise gradient of toluene:EtOAc (100:0, 90:10, 80:20, 60:40 and 40:60) as eluent to give 277 mg (87%) of the sub-title compound.

Workup

  1. customto reach room temperature
  2. customThe pyridine was removed by evaporation
  3. customthe residue was partitioned between water and EtOAc
  4. customThe phases was separated
  5. extractionthe water phase was extracted twice with EtOAc
  6. washthe combined organic phase was washed once with 1M KHSO4, brine
  7. dry with materialdried (Na2SO4)
  8. customThe solvent was evaporated
  9. customthe residue was subjected to purification by flash chromatography

Sources & evidence

ORD record
ord-271f1c96ccb64c6791bf5e8dd395f479
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

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