Ammonia → 2-Amino-5-(4-methoxy-benzoyl)-benzenesulfinamide

HRID 873625Notes

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

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-b4aba0c687b845b59f6cd8f58100ff60
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975439B2

Reaction notes

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