Ammonia → 2-Amino-5-(4-methoxy-benzoyl)-benzenesulfinamide
Reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:18]([NH2:21])(=O)=[O:19].[NH3:22]>O1CCOCC1>[NH2:22][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:18]([NH2:21])=[O:19]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 2-fluoro-5-(4-methoxy-benzoyl)-benzenesulfonamide (0.25 g, 0.81 mmol) dissolved in dioxane (3 mL) is added aqueous ammonia solution (1 mL). The reaction mixture is heated at 100° C. for 6 h in sealed tube and then cooled to room temperature and concentrated in vacuo. The residue is partitioned between water and ethyl acetate, and the aqueous phase is extracted with ethyl acetate three times. The combined organic extracts are washed with a saturated sodium chloride solution, dried with magnesium sulfate, and concentrated in vacuo to provide 0.2 g (81%) of the title compound as a pale yellow solid. 1H NMR (DMSO): δ 8.05 (d, J=2 Hz, 1H), 7.70 (m, 3H), 7.40 (s, 2H), 7.05 (d, J=9 Hz, 2H), 6.92 (d, J=9 Hz, 1H), 3.88 (s, 3H).
Workup
- temperaturecooled to room temperature
- concentrationconcentrated in vacuo
- customThe residue is partitioned between water and ethyl acetate
- extractionthe aqueous phase is extracted with ethyl acetate three times
- washThe combined organic extracts are washed with a saturated sodium chloride solution
- dry with materialdried with magnesium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-1cebe7edeb3b4567bf9d8241d5d9f233
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362063B2
Reaction notes
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