Benzenesulfonamide → 4-Iodo-N-(phenylsulfonyl)benzamide

HRID 55301

Reaction equation

HRID 55301 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[C:11]1([S:17]([NH2:20])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[C:11]1([S:17]([NH:20][C:6](=[O:8])[C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:10][CH:9]=2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 7370BenzenesulfonamideHCID 120854-Iodobenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Product 1

HCID 44868314-Iodo-N-(phenylsulfonyl)benzamideYield 40.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

5 g of 4-iodobenzoic acid is added to a solution of 3.3 g of benzenesulfonamide, 2.68 g of 4-dimethylaminopyridine and 4.04 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide in 100 ml of dichloromethane, and the suspension is stirred for 18 hours at room temperature. The reaction mixture is diluted with 400 ml of dichloromethane, washed in succession with 400 ml portions of 10% hydrochloric acid, water and saturated common salt solution, the organic phase is dried on sodium sulfate and concentrated by evaporation. The residue is suspended in diethyl ether/ethyl acetate=1/1, and the crystallizate is suctioned off. 3.15 g of N-benzenesulfonyl-4-iodobenzoic acid amide of melting point 192°-193° C. is obtained.

Workup

  1. washwashed in succession with 400 ml portions of 10% hydrochloric acid, water and saturated common salt solution
  2. customthe organic phase is dried on sodium sulfate
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b52ab99c986e4c808f849a844c91cd95
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Linked notes

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