Triethylamine → 3-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]-benzenesulfonic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-methylethylamide]
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])=[C:4]([C:22]([F:25])([F:24])[F:23])[CH:3]=1.C(N(CC)CC)C.[OH:33][CH:34]([CH:38]1[CH2:42][O:41][C:40]([CH3:44])([CH3:43])[O:39]1)[CH2:35][NH:36][CH3:37]>O1CCCC1>[OH:33][CH:34]([CH:38]1[CH2:42][O:41][C:40]([CH3:44])([CH3:43])[O:39]1)[CH2:35][N:36]([CH3:37])[S:18]([C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([S:9](=[O:11])(=[O:10])[NH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[C:22]([F:25])([F:24])[F:23])[CH:13]=1)(=[O:20])=[O:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
8.36 g (20 mmol) of 3-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]-benzenesulfonic acid chloride is dissolved in 40 ml of tetrahydrofuran, 2.52 g (25 mmol) of triethylamine and 4.03 (25 mmol) of 2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-methylethylamine are added and stirred for 3 hours at 45° C. The reaction mixture is then concentrated by evaporation under reduced pressure, the residue is extracted with ethyl acetate and the extract is chromatographed on silica gel 60 (Merck) with ethyl acetate/hexane. 9.35 g (16.8 mmol)=84% of the theoretical yield is obtained as an amorphous solid.
Workup
- concentrationThe reaction mixture is then concentrated by evaporation under reduced pressure
- extractionthe residue is extracted with ethyl acetate
- customthe extract is chromatographed on silica gel 60 (Merck) with ethyl acetate/hexane
- custom9.35 g (16.8 mmol)=84% of the theoretical yield
- customis obtained as an amorphous solid
Sources & evidence
- ORD record
- ord-a76d1f7cf3dc40a2aff7c1ef54e73eb8
- Source dataset
- uspto-grants-1992_07
- Patent number
- US05130119
Reaction notes
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