Hydrochloric Acid → 4'-[(Benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonic acid

HRID 29495

Reaction equation

HRID 29495 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([OH:12])=O.C(Cl)(=O)C(Cl)=O.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([S:32]([OH:35])(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.C(N(CC)C(C)C)(C)C.Cl>C1COCC1.CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([S:32]([OH:35])(=[O:33])=[O:34])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)=[O:12]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10331Benzofuran-2-carboxylic acidHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 957994-Biphenylsulfonic acid, 4'-amino-

Product 1

HCID 860588634'-[(Benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonic acidYield 85.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzofuran-2-carboxylic acid (310 mg, 1.9 mmol) was mixed with 3 ml of oxalyl chloride and refluxed for 1 h in the presence of a catalytic amount of DMF, then the excess oxalyl chloride was removed by vacuum. The residue was dissolved in 4 ml of dichloromethane and was added to a mixture of 400 mg (1.6 mmol) of 4′-amino-biphenyl-4-sulfonic acid, N,N-diisopropylethylamine (0.92 ml, 4 eq) and 4 ml of THF in an ice/water bath. The mixture was stirred at room temperature for 4 h. The reaction mixture was mixed with 2N HCl and in the process a suspension formed. The solid was collected by centrifugation and was washed with chloroform and 2N HCl to provide 540 mg of 4′-[(benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonic acid, obtained as pale brown solid.

Workup

  1. customthe excess oxalyl chloride was removed by vacuum
  2. dissolutionThe residue was dissolved in 4 ml of dichloromethane
  3. customformed
  4. customThe solid was collected by centrifugation
  5. washwas washed with chloroform and 2N HCl

Sources & evidence

ORD record
ord-9819ee79efa94489b7bfb2daf8fac508
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Linked notes

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