Pyridine → 4-Iodo-N-(thiazol-2-yl)benzenesulfonamide

HRID 1644635Notes

Reaction equation

HRID 1644635 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[I:7][C:8]1[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.N1C=CC=CC=1.C(Cl)Cl>>[I:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 21552-AminothiazoleHCID 6344DichloromethaneHCID 73994-Iodobenzenesulfonyl chloride

Product 1

HCID 10193184-Iodo-N-(thiazol-2-yl)benzenesulfonamideYield 54.8%

Procedure

2-Aminothiazole (1.32 g, 0.0132 mol) was added to a solution of 4-iodobenzenesulfonyl chloride (4.00 g, 0.0132 mol) in Pyridine (10 mL, 0.1 mol) and methylene chloride (36 mL, 0.56 mol). After stirring 4 d, the reaction mixture was concentrated in vacuo. The resulting oil was taken up in 1:1 methylene chloride-methanol and stirred. A white precipitate formed. The solid was collected by filtration. 2.65 g (49%) of the product was obtained as an off-white solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. stirringstirred
  3. customA white precipitate formed
  4. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-c8baab39655e4a16a230e52354dfcb9d
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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