P-Toluenesulfonamide → HCID 131717833, compound

HRID 1614483Notes

Reaction equation

O.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[CH:14]1[CH:19]=[C:18]2[C:20]([C:22]3[C:27]([C:28](=[O:29])[C:17]2=[CH:16][CH:15]=1)=[C:26]([NH2:30])[C:25]([S:31]([O-:34])(=[O:33])=[O:32])=[CH:24][C:23]=3Br)=[O:21].[Na+:36].[C:37]1([CH3:47])[CH:42]=[CH:41][C:40]([S:43]([NH2:46])(=[O:45])=[O:44])=[CH:39][CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+]>O.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Na+:36].[NH2:30][C:26]1[C:27]2[C:28](=[O:29])[C:17]3[C:18](=[CH:19][CH:14]=[CH:15][CH:16]=3)[C:20](=[O:21])[C:22]=2[C:23]([NH:46][S:43]([C:40]2[CH:39]=[CH:38][C:37](=[CH2:47])[CH2:42][CH:41]=2)(=[O:44])=[O:45])=[CH:24][C:25]=1[S:31]([O-:34])(=[O:32])=[O:33]

Participants

Conditions

Temperature: 70 °C

Procedure

Copper (II) acetate monohydrate (0.13 g, 0.00064 mol) and glucose monohydrate (1.6 g, 0.008 mol) are added to a mixture of bromaminic acid sodium salt (38.2 g, 0.1 mol) and p-toluenesulphonamide (18.8 g 0.11 mol) in water (250 mol) 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 five hours. The resulting mixture is diluted to a volume of 750 ml with water 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 97% yield 1-amino-4-(4'-methlylphenylsulphonamido)-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-28b472b8e83b40bbaf214a7ecca04933
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05196553

Reaction notes

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