Aziridine → 1-[4-[(Methylsulfonyl)amino]benzoyl]aziridine
Reaction equation
ClC(OCC)=O.C([N:9]([CH2:12][CH3:13])CC)C.[CH3:14][S:15]([NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][CH:20]=1)(=[O:17])=[O:16].N1CC1>CC(C)=O>[CH3:14][S:15]([NH:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([N:9]2[CH2:12][CH2:13]2)=[O:25])=[CH:26][CH:27]=1)(=[O:16])=[O:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
To a solution of 0.343 g (3.16 mmol) of ethyl chloroformate in 0.6 mL of acetone cooled to -10° C. under a nitrogen atmosphere add dropwise a solution of 1.0 g (3.16 mmol) of 4-[(methylsulfonyl)amino]benzoic acid triethylamine salt in 25 mL of acetone. Stir the mixture at -10° C. for 2 h then add slowly a solution of 0.136 g (3.16 mmol) of aziridine in 10 mL of acetone. Stir the reaction mixture for 30 min at ambient temperature after the addition is completed then remove the solvent in vacuo. Flash chromatograph the residue on silica gel with diethyl ether: methylene chloride (2:1), evaporate the solvent from the product containing fractions to obtain the title compound.
Workup
- stirringStir the reaction mixture for 30 min at ambient temperature
- additionafter the addition
- customis completed then remove the solvent in vacuo
- customFlash chromatograph the residue on silica gel with diethyl ether: methylene chloride (2:1), evaporate the solvent from the product
- additioncontaining fractions
Sources & evidence
- ORD record
- ord-13065a408ff14803a59f1d7169f2735a
- Source dataset
- uspto-grants-1990_02
- Patent number
- US04900841
Reaction notes
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