Hydrochloric Acid → HCID 17838654, compound
Reaction equation
[CH:1]1[C:6](N)=[CH:5][CH:4]=[C:3]([S:8]([NH:11][C:12]2[S:16][CH:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:2]=1.[ClH:17].N([O-])=O.[Na+].[S:22](=[O:24])=[O:23]>C(O)(=O)C.O>[Cl:17][S:22]([C:6]1[CH:5]=[CH:4][C:3]([S:8]([NH:11][C:12]2[S:16][CH:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:2][CH:1]=1)(=[O:24])=[O:23]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
5.2 g (20.4 mmol) of sulfathiazole was added to a mixed solution of 14 ml of water and 3.4 ml of concentrated hydrochloric acid and the mixture was stirred. To the mixture was added dropwise an aqueous saturated solution of 2.1 g (30.4 mmol) of sodium nitrite at 0° C. or less. Then, 5 ml of acetic acid was added thereto, followed by stirring at 5° C. for about 10 minutes. An acetic acid solution saturated with sulfur dioxide (solution prepared by saturating 18 ml of acetic acid with sulfur dioxide and then adding 830 mg of cupric chloride.dihydrate thereto) was added dropwise to the reaction solution at 0° C. under stirring. After 5 minutes, the reaction solution was poured into ice-water. The precipitates were collected by filtration, washed with water and dried, to give 2.9 g of 4-chlorosulfonyl-N-(2-thiazolyl)benzenesulfonamide. 570 mg (1.68 mmol) of the product was reacted with 200 mg (1.2 mmol) of the compound of Production Example 1a in the same manner as in Production Example 4a and treated, to give 456 mg of the title compound.
Workup
- stirringby stirring at 5° C. for about 10 minutes
- concentrationby saturating 18 ml of acetic acid with sulfur dioxide
- additionadding 830 mg of cupric chloride
- additiondihydrate thereto) was added dropwise to the reaction solution at 0° C.
- stirringunder stirring
- additionthe reaction solution was poured into ice-water
- filtrationThe precipitates were collected by filtration
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-5661a8815c5c4deba2488411ac8e8baa
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834049B2
Reaction notes
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