Cesium carbonate → 4-[4-Methyl-2-([1,3,4]thiadiazol-2-ylamino)-thiazol-5-yl]-benzenesulfonamide

HRID 908157Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].C[C:8]1[S:12][C:11]([NH2:13])=[N:10][N:9]=1.Cl[C:15]1[S:16][C:17]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)=[C:18]([CH3:20])[N:19]=1.C(OCC)(=O)C.CO>CC(N(C)C)=O>[CH3:20][C:18]1[N:19]=[C:15]([NH:13][C:11]2[S:12][CH:8]=[N:9][N:10]=2)[S:16][C:17]=1[C:21]1[CH:22]=[CH:23][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Caesium carbonate (0.08 g, 0.24 mmol) and 5-methyl-[1,3,4]thiadiazol-2-ylamine (0.031 g, 0.27 mmol) are added to a solution of 4-(2-chloro-4-methyl-thiazol-5-yl)-benzenesulfonamide (25d) (0.07 g, 0.24 mmol) in dimethylacetamide (2 ml). The mixture is heated with stirring at 110° C. for 18 hours. After adding more 5-methyl-[1,3,4]thiadiazol-2-ylamine (0.056 g, 0.49 mmol) heating is continued at 130° C. for an additional 8 hours. The solvent is removed and the product is purified by chromatography on silica eluting with ethyl acetate to give an orange solid. Trituration with ethyl acetate-methanol affords the title compound as a yellow solid (0.0081 g)

Workup

temperatureThe mixture is heated
temperatureheating
waitis continued at 130° C. for an additional 8 hours
customThe solvent is removed
customthe product is purified by chromatography on silica eluting with ethyl acetate
customto give an orange solid

Sources & evidence

ORD record: ord-932366fa9fdf4f6d94af2f0ec1f72f89
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017608B2

Reaction notes

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