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

HRID 1644636Notes

Reaction equation

HRID 1644636 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[S:14][CH:15]=[CH:16][N:17]=1>N1C=CC=CC=1>[I:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][C:13]2[S:14][CH:15]=[CH:16][N:17]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 73994-Iodobenzenesulfonyl chloride

Product 1

HCID 10193184-Iodo-N-(thiazol-2-yl)benzenesulfonamideYield 53.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Iodobenzenesulfonyl chloride (1.8 g, 6.0 mmol, 1.0 equiv) was added portion-wise to a 0° C. solution of 2-aminothiazole (654 mg, 6.53 mmol, 1.1 equiv) in 4.91 mL of anhydrous pyridine. After addition was complete, the reaction mixture was warmed to ambient temperature. After 3 d, the reaction mixture was concentrated in vacuo. The residue was treated with methanol and ether to precipitate the product. The solid was collected by filtration, washing with ether, to afford the product as a light brown solid (1.18 g, 49%).

Workup

  1. additionAfter addition
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additionThe residue was treated with methanol and ether
  4. customto precipitate the product
  5. filtrationThe solid was collected by filtration
  6. washwashing with ether

Sources & evidence

ORD record
ord-27ac1ea4cfac4afc8bca94b3a51c6756
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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