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Benzenesulfonamide → Sodium 1-amino-4-[(benzenesulfonyl)amino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate

HRID 1614484
Notes
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Reaction equation

HRID 1614484 reaction equation
O.OC1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O.[CH:25]1[CH:30]=[C:29]2[C:31]([C:33]3[C:38]([C:39](=[O:40])[C:28]2=[CH:27][CH:26]=1)=[C:37]([NH2:41])[C:36]([S:42]([O-:45])(=[O:44])=[O:43])=[CH:35][C:34]=3Br)=[O:32].[Na+:47].[C:48]1([S:54]([NH2:57])(=[O:56])=[O:55])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+]>O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Na+:47].[NH2:41][C:37]1[C:38]2[C:39](=[O:40])[C:28]3[C:29](=[CH:30][CH:25]=[CH:26][CH:27]=3)[C:31](=[O:32])[C:33]=2[C:34]([NH:57][S:54]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)(=[O:56])=[O:55])=[CH:35][C:36]=1[S:42]([O-:45])(=[O:44])=[O:43]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 7370BenzenesulfonamideHCID 10340Sodium CarbonateHCID 62223Lactose, monohydrateHCID 516892Sodium BicarbonateHCID 5076555Bromamine acid sodium salt

Product 1

HCID 23672954
Sodium 1-amino-4-[(benzenesulfonyl)amino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate
Yield 95%

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

Copper (II) sulphate pentahydrate (0.16 g, 0.00064 mol) and lactose monohydrate (2.9 g, 0.008 mol) are added to a mixture of bromaminic acid sodium salt (38.2 g, 0.1 mol) and benzene sulphonamide (17.3 g, 0.11 mol) in water (250 ml) containing sodium carbonate (3.8 g) and sodium bicarbonate (19.0 g). The mixture which has a pH of 8.5-9.0, is heated to 70° C. and stirred at this temperature for 5 hours. The resulting mixture is diluted with water to a volume of 750 ml and cooled to 40° C. The solid product is filtered off and washed with a solution of sodium chloride (12 g) in water (1300 ml) to give a 95% yield of 1-amino-4-phenylsulphonamido-anthraquinone-2-sulphonic acid sodium salt, a product of formula I where M denotes sodium and R denotes a group of formula III.

Workup

  1. temperaturecooled to 40° C
  2. filtrationThe solid product is filtered off
  3. washwashed with a solution of sodium chloride (12 g) in water (1300 ml)

Sources & evidence

ORD record
ord-aa5311e19df3447097238bd2b0f18c4b
Source dataset
uspto-grants-1993_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05196553

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes