Pyridine → Phenyl 4-(ethylsulfonamidomethyl)phenylcarbamate
Reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][NH:7][S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23]>C(#N)C.O1CCCC1>[CH2:11]([S:8]([NH:7][CH2:6][C:5]1[CH:13]=[CH:14][C:2]([NH:1][C:22](=[O:23])[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH3:12]Participants
6
Procedure
N-(4-Aminobenzyl)ethanesulfonamide (504 mg, 2.35 mmol) was dissolved in acetonitrile (3 mL) and tetrahydrofuran (4 mL). The reaction mixture was added pyridine (0.23 mL, 2.78 mmol) and phenyl chloroformate (0.31 mL, 2.43 mmol) and stirred at room temperature for 3 h under nitrogen atmosphere. TLC showed complete consumption of starting material. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic part was washed with water and brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crude was purified by column chromatography to give phenyl 4-(ethylsulfonamidomethyl)phenylcarbamate (697 mg, 87%).
Workup
- customconsumption of starting material
- additionThe reaction mixture was diluted with water
- extractionextracted with ethyl acetate
- washThe organic part was washed with water and brine
- dry with materialThe organic layer was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe crude was purified by column chromatography
Sources & evidence
- ORD record
- ord-acd089da99c04ca696f32be790e2eb73
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937092B2
Reaction notes
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