Triethylamine → 4-[2-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]acetylamino]benzenesulfonic Acid

HRID 248747Notes

Reaction equation

HRID 248747 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][C:13]([OH:15])=O)(=[O:11])=[O:10])=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([OH:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1.O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][C:13]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([OH:30])(=[O:28])=[O:29])=[CH:23][CH:22]=2)=[O:15])(=[O:10])=[O:11])=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 8479Sulfanilic acidHCID 10868DicyclohexylcarbodiimideHCID 156765552-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]acetic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 197639954-[2-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]acetylamino]benzenesulfonic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under the conditions of Example 2(a), 3.012 g (10 mmol) of 2-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]acetic acid, 1.732 g (10 mmol) of 4-aminobenzenesulfonic acid, 1.531 g (10 mmol) of hydroxybenzotriazole, hydrate, as well as 1.012 g (10 mmol) of triethylamine and 2.063 g (10 mmol) of dicyclohexylcarbodiimide are reacted and worked up analogously. The crude product is dissolved in distilled water, extracted with ethyl acetate, and converted into the free acid by treatment with acidic cation exchanger, thus obtaining the title compound by freeze-drying of the aqueous solution.

Workup

  1. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-b95fea6ea28f428c8f5b2ec8d40e39c2
Source dataset
uspto-grants-1993_05
Patent number
US05210290

Reaction notes

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