Hydrochloric Acid → 3-cyano-4-(2-bromo-6-methyl-phenoxy)-N-[1,2,4]thiadiazol-5-yl-benzenesulfonamide

HRID 1692247Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].C([O-])([O-])=O.[K+].[K+].[C:16]([C:18]1[CH:19]=[C:20]([S:25]([NH:28][C:29]2[S:33][N:32]=[CH:31][N:30]=2)(=[O:27])=[O:26])[CH:21]=[CH:22][C:23]=1F)#[N:17].Cl>CN(C=O)C>[C:16]([C:18]1[CH:19]=[C:20]([S:25]([NH:28][C:29]2[S:33][N:32]=[CH:31][N:30]=2)(=[O:27])=[O:26])[CH:21]=[CH:22][C:23]=1[O:9][C:3]1[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])#[N:17]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-bromo-6-methylphenol (6.0 mmol, 1120 mg) and K2CO3 (10.5 mmol, 1450 mg) in DMF (15.0 mL) was added 3-cyano-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (Preparation 65, 4.5 mmol, 1280 mg). The reaction mixture was heated at 80° C. After stirring for overnight at 80° C., the reaction was cooled to room temperature and poured into 1 N aqueous HCl (100 mL) to precipitate which was filtered to obtain solid. The solid was washed with water (100 mL) and heptane (100 mL) and the solid was dried under vacuum to furnish the title compound. LCMS Rt=3.05 minutes MS m/z 451 [M(79Br)H]+, 453 [M(81Br)H]+ 1HNMR (d6-DMSO): δ 2.17 (s, 3H), 6.70 (d, 1H), 7.25-7.31 (m, 1H), 7.44-7.48 (m, 1H), 7.64-7.69 (m, 1H), 8.01 (dd, 1H), 8.34 (d, 1H), 8.52 (s, 1H).

Workup

temperaturethe reaction was cooled to room temperature
customto precipitate which
filtrationwas filtered
customto obtain solid
washThe solid was washed with water (100 mL) and heptane (100 mL)
customthe solid was dried under vacuum

Sources & evidence

ORD record: ord-e44ba994cd1748a5817c9bfedf3e8edc
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153814B2

Reaction notes

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