Reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:12]=[C:13]([NH2:16])[S:14][CH:15]=2)[CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3].[Cl:17][C:18]1[CH:19]=[C:20]([S:25](Cl)(=[O:27])=[O:26])[CH:21]=[CH:22][C:23]=1[Cl:24].Cl>N1C=CC=CC=1>[Cl:17][C:18]1[CH:19]=[C:20]([S:25]([NH:16][C:13]2[S:14][CH:15]=[C:11]([C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=3)[N:12]=2)(=[O:26])=[O:27])[CH:21]=[CH:22][C:23]=1[Cl:24]Participants
Procedure
A mixture of 0.5 g of 4-(3-nitro-phenyl)-thiazol-2-ylamine hydrochloride with 0.52 g of 3,4-dichlorobenzenesulfonyl chloride was stirred overnight with 2 ml of pyridine. The resulting, red colored suspension was poured into 25 ml of 1N hydrochloric acid and the solid which thereby separated was filtered off and dissolved in a mixture of 30 ml of ethanol and 20 ml of 2N sodium hydroxide solution. After the addition of 0.5 g of active charcoal the mixture was stirred at room temperature for 30 minutes and subsequently the active charcoal was filtered off. The product separated upon neutralization with concentrated hydrochloric acid. Recrystallization from 80 ml of 50% ethanol yielded 0.39 g of 3,4-dichloro-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide as yellowish crystals.
Workup
- customthe solid which thereby separated
- filtrationwas filtered off
- dissolutiondissolved in a mixture of 30 ml of ethanol and 20 ml of 2N sodium hydroxide solution
- additionAfter the addition of 0.5 g of active charcoal the mixture
- filtrationsubsequently the active charcoal was filtered off
- customThe product separated upon neutralization with concentrated hydrochloric acid
- customRecrystallization from 80 ml of 50% ethanol
Sources & evidence
- ORD record
- ord-9eb2dc07101942c9a7c87711103fa45f
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05958910
Linked notes
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