Benzenesulfonyl chloride → HCID 22033475, compound

HRID 1791860Notes

Reaction equation

HRID 1791860 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([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:3]=1.[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][O:9][C:4]2[CH:3]=[C:2]([NH:1][S:26]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:28])=[O:27])[CH:7]=[C:6]([CH3:8])[CH:5]=2)=[CH:17][CH:16]=1)#[N:19]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 22033482HCID 22033482, compound

Product 1

HCID 22033475HCID 22033475, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cold solution (ice:water temperature) of amino-[3-2-(4-cyanophenyl)ethoxy]-5-methylbenzene (0.13 g; 0.50 mmol; from step (iii) above) in pyridine (5 mL) was added benzenesulfonyl chloride (71 μL; 0.55 mmol). After 2 hours stirring, NaHCO3/aq (sat.) was added, and the solution extracted with EtOAc. The combined organic phases were dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography (SiO2; EtOAc:heptane (1:1)) to give 0.19 g (97%) of the sub-title compound.

Workup

  1. extractionthe solution extracted with EtOAc
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by flash chromatography (SiO2; EtOAc:heptane (1:1))

Sources & evidence

ORD record
ord-d2f2a62a9a7f4a4bbe47ffbd989c1976
Source dataset
uspto-grants-2006_07
Patent number
US07074820B2

Reaction notes

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