2,3-Dichlorobenzene-1-sulfonyl chloride → 2-Acetylamino-4-[4-(2,3-dichlorobenzenesulphonylamino)phenyl]-1H-pyrrole-3-carboxamide
Reaction equation
[C:1]([NH:4][C:5]1[NH:6][CH:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[C:9]=1[C:10]([NH2:12])=[O:11])(=[O:3])[CH3:2].[Cl:20][C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1>[C:1]([NH:4][C:5]1[NH:6][CH:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][S:28]([C:22]3[CH:23]=[CH:24][CH:25]=[C:26]([Cl:27])[C:21]=3[Cl:20])(=[O:30])=[O:29])=[CH:15][CH:14]=2)[C:9]=1[C:10]([NH2:12])=[O:11])(=[O:3])[CH3:2]Participants
4
Procedure
A suspension of 70 mg (0.271 mmol) of 2-acetylamino-4-(4-aminophenyl)-1H-pyrrole-3-carboxamide and 70 mg (0.285 mmol) of 2,3-dichlorobenzene-sulphonyl chloride in 1.5 cm3 of pyridine is stirred at room temperature for 24 hours and then the reaction medium is evaporated to dryness under reduced pressure. The crude product is purified by flash chromatography [eluent; dichloromethane/methanol (97/3 by volume)]. After concentrating under reduced pressure the fractions containing the expected product, 22 mg of 2-acetylamino-4-[4-(2,3-dichlorobenzenesulphonylamino)phenyl]-1H-pyrrole-3-carboxamide are obtained in the form of a beige solid melting at 265° C.
Workup
- customthe reaction medium is evaporated to dryness under reduced pressure
- customThe crude product is purified by flash chromatography [eluent; dichloromethane/methanol (97/3 by volume)]
- concentrationAfter concentrating under reduced pressure the fractions
- additioncontaining the expected product, 22 mg of 2-acetylamino-4-[4-(2,3-dichlorobenzenesulphonylamino)phenyl]-1H-pyrrole-3-carboxamide
Sources & evidence
- ORD record
- ord-4eb77725a27b4e64aeb9a0b37e5f4096
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592365B2
Reaction notes
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