Chloroform → Quinoline-8-sulfonyl bromide

HRID 460762Notes

Reaction equation

HRID 460762 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11](NN)(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)Cl.[Br:20]Br>CCCCCC>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11]([Br:20])(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24408Bromine3×HCID 747844HCID 747844, compound

Product 1

HCID 21394670Quinoline-8-sulfonyl bromideYield 749.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A 500 ml, single-neck flask equipped with a magnetic stirrer is charged with 6.59 g (0.0295 mol) of 8-quinolinesulfonyl hydrazine and 200 ml of chloroform. Crushed ice is added, and the slurry is vigorously stirred. 9.50 g of bromine is added dropwise to the slurry with stirring. After the addition of bromine is complete and all of the bromine color has disappeared, the layers are separated. The chloroform layer is dried over anhydrous magnesium sulfate, and the chloroform is removed in vacuo leaving a pale yellow solid. The solid is slurried with hexane, filtered, and vacuum dried to give 6.00 g (0.221 mol) of 8-quinolinesulfonyl bromide m.p. 142°-144° C.

Workup

  1. customA 500 ml, single-neck flask equipped with a magnetic stirrer
  2. additionCrushed ice is added
  3. stirringwith stirring
  4. customthe layers are separated
  5. dry with materialThe chloroform layer is dried over anhydrous magnesium sulfate
  6. customthe chloroform is removed in vacuo
  7. customleaving a pale yellow solid
  8. filtrationfiltered
  9. customvacuum dried

Sources & evidence

ORD record
ord-183da4bc39884f4aaefd337203b68ba7
Source dataset
uspto-grants-1977_12
Patent number
US04061639

Reaction notes

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