Oxalyl chloride → 4'-[(Benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonyl chloride
Reaction equation
C(Cl)(=O)C([Cl:4])=O.[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[C:8]1[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([S:31]([OH:34])(=O)=[O:32])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)=[O:17]>CN(C=O)C>[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[C:8]1[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([S:31]([Cl:4])(=[O:34])=[O:32])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)=[O:17]Participants
4
Procedure
To 75 ml of DMF cooled to −20° C., oxalyl chloride (6.7 ml, 76 mmol) was carefully added dropwise. A white suspension was formed and the fumes generated were removed by blowing N2 through the flask. A solution of 4′-[(benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonic acid (15 g, 38 mmol) in 100 ml DMF was added slowly and the temperature was maintained <0° C. After the addition was complete, the reaction mixture was warmed to room temperature and was stirred at room temperature for 3 h. The reaction mixture was poured into 4L ice/water, and the suspension was filtered. The solid was collected and dried under vacuum to provide 7.3 g of 4′-[(benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonyl chloride, obtained as off-white solid.
Workup
- customA white suspension was formed
- customthe fumes generated were removed
- temperaturethe temperature was maintained <0° C
- additionAfter the addition
- filtrationthe suspension was filtered
- customThe solid was collected
- customdried under vacuum
Sources & evidence
- ORD record
- ord-784ee4c591ce4838889d691a7b73d313
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07420001B2
Reaction notes
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