P-Toluenesulfonamide → 64981-00-6

HRID 1614485Notes

Reaction equation

Cl.NO.[CH:4]1[CH:9]=[C:8]2[C:10]([C:12]3[C:17]([C:18](=[O:19])[C:7]2=[CH:6][CH:5]=1)=[C:16]([NH2:20])[C:15]([S:21]([O-:24])(=[O:23])=[O:22])=[CH:14][C:13]=3Br)=[O:11].[Na+:26].[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33]([NH2:36])(=[O:35])=[O:34])=[CH:29][CH:28]=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+:26].[NH2:20][C:16]1[C:17]2[C:18](=[O:19])[C:7]3[C:8](=[CH:9][CH:4]=[CH:5][CH:6]=3)[C:10](=[O:11])[C:12]=2[C:13]([NH:36][S:33]([C:30]2[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=2)(=[O:34])=[O:35])=[CH:14][C:15]=1[S:21]([O-:24])(=[O:22])=[O:23]

Participants

Conditions

Temperature: 70 °C

Procedure

Copper (II) sulphate pentahydrate (0.122 g, 0.0005 mol) and hydroxylamine hydrochloride (1.12 g, 0.016 mol) are added to a mixture of bromaminic acid sodium salt (38.2 g, 0.1 mol) and p-toluene sulphonamide (18.8 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. for 6 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 94% yield of 1-amino-4-(4'-methylphenylsulphonamido)-anthraquinone-2-sulphonic acid sodium salt, a product of formula I where M denotes sodium and R denotes a group of formula IV.

Workup

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

Sources & evidence

ORD record: ord-f95694bba40d4966a514af20743158f4
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05196553

Reaction notes

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