Iodine → 2-Methoxy-5-[4-methyl-2-(pyrazin-2-ylamino)-thiazol-5-yl]-benzenesulfonamide

HRID 908147Notes

Reaction equation

HRID 908147 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=O)[CH3:11])=[CH:5][C:4]=1[S:13]([NH2:16])(=[O:15])=[O:14].[N:17]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[NH:23][C:24]([NH2:26])=[S:25].II>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:25][C:24]([NH:23][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][N:17]=3)=[N:26][C:10]=2[CH3:11])=[CH:5][C:4]=1[S:13]([NH2:16])(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 807IodineHCID 2771013N-PyrazinylthioureaHCID 141797592-Methoxy-5-(2-oxopropyl)benzenesulfonamide

Product 1

HCID 866062082-Methoxy-5-[4-methyl-2-(pyrazin-2-ylamino)-thiazol-5-yl]-benzenesulfonamideYield 22.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Methoxy-5-(2-oxo-propyl)-benzenesulfonamide (S. Sakurai et al. Chem. Pharm. Bull. 40(6) 1443-1451 (1992)) (0.3 g, 1.23 mmol), pyrazin-2-yl-thiourea (0.19 g, 1.23 mmol), iodine (0.31 g, 1.23 mmol) in pyridine (2.5 ml) is stirred at 60° C. for 20 hours. The mixture is concentrated. To the residue is added water, the precipitate is collected and recrystallised from ethanol to give the titled compound (0.103 g). m.p. 378.2° C.

Workup

  1. concentrationThe mixture is concentrated
  2. additionTo the residue is added water
  3. customthe precipitate is collected
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-759108d047014d5db430b3c5c1edaab4
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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