Pyridine → Phenyl 4-(methylsulfonamidomethyl)phenylcarbamate

HRID 1428710Notes

Reaction equation

HRID 1428710 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22]>C(#N)C.O1CCCC1>[CH3:11][S:8]([NH:7][CH2:6][C:5]1[CH:12]=[CH:13][C:2]([NH:1][C:21](=[O:22])[O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 12822521HCID 12822521, compound

Product 1

HCID 86679364Phenyl 4-(methylsulfonamidomethyl)phenylcarbamateYield 78%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(4-Aminobenzyl)methanesulfonamide (352 mg, 1.76 mmol) was dissolved in acetonitrile (3 mL) and tetrahydrofuran (4 mL). The reaction mixture was added pyridine (0.17 mL, 2.11 mmol) and phenyl chloroformate (0.23 mL, 1.85 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-(methylsulfonamidomethyl)phenylcarbamate (438 mg, 78%).

Workup

  1. customconsumption of starting material
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic part was washed with water and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-cddda5fa52204ba8907dfc7959d86be5
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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