Benzenesulfonyl chloride → Benzenesulfonamide

HRID 903088

Reaction equation

HRID 903088 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:11]C1C=CC2C(=O)C3C(=CC=CC=3)C(=O)C=2C=1>N1C=CC=CC=1>[C:4]1([S:7]([NH2:11])(=[O:9])=[O:8])[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 83412-Aminoanthraquinone

Product 1

HCID 7370Benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

1.32 mol (166 cm3) of benzenesulfochloride is added little by little at 45° C. with constant stirring to a solution of 1 mol (223 g) of 2-amino anthraquinone in 1800 cm3 of pyridine. When the addition is complete the reaction mixture is kept at 45° C. for 4 hours. It is then cooled to 0° C. Drying yields the crude product which is then washed successively in slightly hydrochloric water, in water, and in alcohol. 320 g of practically pure benzene-sulfonamide are thus obtained, which melt at 276° C. 12 g of slightly less pure benzene-sulfonamide may be recovered from the pyridine filtrate by dilution.

Workup

  1. additionWhen the addition
  2. customDrying
  3. customyields the crude product which
  4. washis then washed successively in slightly hydrochloric water, in water

Sources & evidence

ORD record
ord-58308ea7751b41fb88b6ba80bb7190d6
Source dataset
uspto-grants-1980_10
Patent number
US04226784

Linked notes

Loading…