Ammonium Hydroxide → HCID 86657437, compound
Reaction equation
[F:1][C:2]([F:19])([F:18])[S:3]([NH:6][S:7]([C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=1Br)(=[O:9])=[O:8])(=[O:5])=[O:4].[Na].[OH-:21].[NH4+:22].[Na][Na]>C(O)CC.[Cu].CN(C=O)C>[F:1][C:2]([F:19])([F:18])[S:3]([NH:6][S:7]([C:10]1[C:11]([C:11]2[C:10]([S:7]([NH:22][S:3]([C:2]([F:1])([F:18])[F:19])(=[O:5])=[O:4])(=[O:8])=[O:21])=[CH:15][C:14]([Br:16])=[CH:13][CH:12]=2)=[CH:12][CH:13]=[C:14]([Br:16])[CH:15]=1)(=[O:9])=[O:8])(=[O:5])=[O:4]Participants
Conditions
- Temperature
- 120 °C
Procedure
Inside a glove box, a 200 mL round-bottom flask equipped with a stirring bar, reflux condenser, and a septum was charged with N-trifluoromethanesulfonyl-2,5-dibromo-benzene-sulfonamide, sodium salt (11.24 g, 24 mmoles), activated copper powder (23.5 g), and DMF (50 mL). The flask was heated to 120° C. under nitrogen and stirred overnight. The solution was cooled to room temperature, filtered, and the solids washed with DMF. The solvent was evaporated by distilling under high vacuum and the resulting solids were dried under vacuum. The solids were dissolved in water by adding hydrochloric acid to give a pH of 2-3. Residual dark solids were filtered off then the solution was heated to a reflux, treated with sodium chloride (30 g), and concentrated to 125 mL to induce precipitation. The mixture was cooled to room temperature to give colored solids. Ammonium hydroxide was added to give a dark blue solution, which removed most of the color from the solids. The solids were collected by vacuum filtration, washed with ether, and dried under vacuum to give 9.02 g (97% crude yield). The solids were dissolved in n-propanol at a reflux, treated with decolorizing carbon, filtered, evaporated, and dried under vacuum. The solids were recrystallized twice from dioxane, dried in a vacuum oven at 150° C. under nitrogen purge, and transferred to a glove box for storage and handling to give 4.195 g (45% yield) of N,N′-bis(trifluoromethanesulfonyl)-4,4′-dibromo-biphenyl-2,2′-disulfonamide, disodium salt. 1H NMR (DMSO-d6): 7.26 (d, J=8.2 Hz, 2H), 7.62 (dd, J=8.2 and 2.2 Hz, 2H), 8.03 (d, J=2.2 Hz, 2H).
Workup
- customInside a glove box, a 200 mL round-bottom flask equipped with a stirring bar
- temperaturereflux condenser
- temperatureThe solution was cooled to room temperature
- filtrationfiltered
- washthe solids washed with DMF
- customThe solvent was evaporated
- distillationby distilling under high vacuum
- customthe resulting solids were dried under vacuum
- dissolutionThe solids were dissolved in water
- additionby adding hydrochloric acid
- customto give a pH of 2-3
- filtrationResidual dark solids were filtered off
- temperaturethe solution was heated to a reflux
- additiontreated with sodium chloride (30 g)
- concentrationconcentrated to 125 mL
- customprecipitation
- temperatureThe mixture was cooled to room temperature
- customto give colored solids
- customto give a dark blue solution, which
- customremoved most of the color from the solids
- filtrationThe solids were collected by vacuum filtration
- washwashed with ether
- customdried under vacuum
- customto give 9.02 g (97% crude yield)
- additiontreated with decolorizing carbon
- filtrationfiltered
- customevaporated
- customdried under vacuum
- customThe solids were recrystallized twice from dioxane
- customdried in a vacuum oven at 150° C. under nitrogen
- custompurge
- customtransferred to a glove box for storage
Sources & evidence
- ORD record
- ord-7f49d2787d8841fc926e5ab4ea2e8539
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08058383B2
Reaction notes
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