3-Pyridylthiourea → 2-Chloro-4-[4-methyl-2-(pyridin-3-ylamino)-thiazol-5-yl]-benzenesulfonamide

HRID 908152Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([NH2:10])=[S:9])[CH:2]=1.Br[CH:12]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[C:18]([Cl:26])[CH:17]=1)[C:13](=O)[CH3:14]>C(O)C>[Cl:26][C:18]1[CH:17]=[C:16]([C:12]2[S:9][C:8]([NH:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[N:10][C:13]=2[CH3:14])[CH:21]=[CH:20][C:19]=1[S:22]([NH2:25])(=[O:24])=[O:23]

Participants

Conditions

Temperature: 60 °C

Procedure

3-Pyridylthiourea (0.047 g, 0.31 mmol) is added to a stirred solution of 4-(1-Bromo-2-oxo-propyl)-2-chloro-benzenesulfonamide (Example 23d) (0.10 g, 0.31 mmol) in ethanol (5 ml). The solution is heated at 60° C. for 3 hours. The solvent is removed and the residue is purified by chromatography on silica eluting with ethyl acetate-hexane to give the title compound (0.020 g).

Workup

customThe solvent is removed
customthe residue is purified by chromatography on silica eluting with ethyl acetate-hexane

Sources & evidence

ORD record: ord-a499e52bf20f48b8a610812c3f4e8aea
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017608B2

Reaction notes

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