Benzenesulfonyl chloride → HCID 15718670, compound

HRID 2165369Notes

Reaction equation

HRID 2165369 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[N:14][CH:15]=[CH:16][C:11]=3[NH:10][CH:9]=2)=[CH:4][CH:3]=1.C([Li])CCC.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1.CCCCCC>[C:22]1([S:28]([N:10]2[C:11]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[CH:9]2)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 15718669HCID 15718669, compoundHCID 178418339Butyllithium

Product 1

HCID 15718670HCID 15718670, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

106 mg (0.5mM) of the product of Step 3, above, in 5 ml of absolute THF is cooled to -78°. 0.328 ml (0.525mM) of 1.6M n-butyllithium in hexane is added and the mixture stirred for 1 hour whilst allowing the temperature to rise to 0°. The mixture is then re-cooled to -60° and 97mg (0.55mM) of benzenesulfonyl chloride is added. After allowing to warm to RT overnight, the mixture is quenched with aqueous NaHCO3 and extracted with ethyl acetate. After washing with NaHCO3 the mixture is dried over Na2SO4 and evaporated to dryness. The residue is triturated with ether and the solids produced precipitated and dried to produce the title product of this step.

Workup

  1. customto rise to 0°
  2. temperatureThe mixture is then re-cooled to -60°
  3. customthe mixture is quenched with aqueous NaHCO3
  4. extractionextracted with ethyl acetate
  5. washAfter washing with NaHCO3 the mixture
  6. dry with materialis dried over Na2SO4
  7. customevaporated to dryness
  8. customThe residue is triturated with ether
  9. customthe solids produced
  10. customprecipitated
  11. customdried

Sources & evidence

ORD record
ord-7bf9a39a77764a5fa10848848d52c2f5
Source dataset
uspto-grants-1990_07
Patent number
US04939159

Reaction notes

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