Reaction equation
Br.[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].[C:17]1([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>N1C=CC=CC=1>[CH2:23]([O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([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:33])=[O:32])=[CH:27][CH:26]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1Participants
5
Procedure
A mixture of 0.5 g of 4-(3-nitro-phenyl)-thiazol-2-ylamine hydrobromide with 0.51 g of 4-phenylmethoxy-benzenesulfonyl chloride was stirred overnight with 2 ml of pyridine. The resulting, red colored suspension was poured into 30 ml of 1N hydrochloric acid. The mixture was extracted three times with ethyl acetate. The organic phases were combined, dried with magnesium sulphate and freed from solvent. The residue was boiled with 30 ml of ethyl acetate, insoluble constituents were filtered off and the solution was treated at boiling with 20 ml of hexane. 0.5 g of 4-benzyloxy-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide separated as beige crystals upon cooling.
Workup
- extractionThe mixture was extracted three times with ethyl acetate
- dry with materialdried with magnesium sulphate
- filtrationwere filtered off
- additionthe solution was treated
- custom0.5 g of 4-benzyloxy-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide separated as beige crystals
- temperatureupon cooling
Sources & evidence
- ORD record
- ord-ec48580dd84b43cfa8d6fe73f01abebc
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05958910
Linked notes
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