Benzenesulfonamide → HCID 66864963, compound

HRID 2061321Notes

Reaction equation

HRID 2061321 reaction equation
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[P:16](Cl)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1>[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]1([PH:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 7370BenzenesulfonamideHCID 66180ChlorodiphenylphosphineHCID 178418339Butyllithium

Product 1

HCID 66864963HCID 66864963, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Commercially available benzenesulfonamide (21.630 mmole, 1 eq) was dissolved in tetrahydrofuran (75 mL). The resulting solution was cooled at 0° C. nBuLi (1.02 eq, commercial solution 2.5 M in hexanes) was added dropwise leading to a white suspension. The suspension was stirred at room temperature for 30 min. The suspension was cooled at 0° C. and commercial Ph2PCl (1.01 eq) was added dropwise. The clear solution obtained was stirred overnight at room temperature. The solvent was then evaporated. The crude product was dissolved in 40 mL of dichloromethane (DCM), and filtered over a plug of SiO2 under argon. The plug was washed 5 times with 20 mL of DCM, and once with 20 mL of ethyl acetate (EA). All organic layers were united and evaporated to a sticky oil. Co-evaporation in Et2O (twice 40 mL) lead to a white powder.

Workup

  1. additionwas added dropwise
  2. temperatureThe suspension was cooled at 0° C.
  3. customThe clear solution obtained
  4. stirringwas stirred overnight at room temperature
  5. customThe solvent was then evaporated
  6. dissolutionThe crude product was dissolved in 40 mL of dichloromethane (DCM)
  7. filtrationfiltered over a plug of SiO2 under argon
  8. washThe plug was washed 5 times with 20 mL of DCM
  9. customevaporated to a sticky oil
  10. customCo-evaporation in Et2O (twice 40 mL) lead to a white powder

Sources & evidence

ORD record
ord-bc759439c0e04056ad743237fb495604
Source dataset
uspto-grants-2012_10
Patent number
US08283276B2

Reaction notes

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