Potassium Carbonate → n-(5-Oxo-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-methanesulfonamide

HRID 1690701Notes

Reaction equation

[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([NH2:14])=[O:13])[CH:5]=[CH:4][C:3]1=2.C([O-])([O-])=O.[K+].[K+].[OH-].[K+].[CH3:23][S:24](Cl)(=[O:26])=[O:25]>O1CCCC1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([NH:14][S:24]([CH3:23])(=[O:26])=[O:25])=[O:13])[CH:5]=[CH:4][C:3]1=2

Participants

Conditions

Temperature: 55 °C

Procedure

A sample of 5-Oxo-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid amide (Example 81, Step 1) (29.4 mg, 0.16 mmol) in tetrahydrofuran (71 μL) is treated with K2CO3 (36.5 mg, 0.26 mmol), powdered KOH (32.9 mg, 0.82 mmol) and tetrabutylammonium hydrogen sulfate (2.6 mg, 0.008 mmol) in that order. The reaction is warmed to 55° C. and vigorously stirred for 20 minutes. Then a solution of methanesulfonyl chloride (23.2 mg, 0.20 mmol) in tetrahydrofuran (140 μL) is added over 20 minutes and the reaction was stirred at 55° C. overnight. The reaction is then cooled to room temperature, diluted with ethyl acetate and extracted with water twice. The organic phase is then dried over MgSO4, filtered and the solvent is removed. The crude sulfonamide (35.5 mg 86% yield) is taken on without purification; LC/MS calculated for [M+H]+ C12H13NO4S: 268.1, found: 268.1.

Workup

stirringthe reaction was stirred at 55° C. overnight
temperatureThe reaction is then cooled to room temperature
extractionextracted with water twice
dry with materialThe organic phase is then dried over MgSO4
filtrationfiltered
customthe solvent is removed

Sources & evidence

ORD record: ord-c63132afab154167a46eb642d69ed1d0
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153671B2

Reaction notes

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