Pyridine → Phenyl 3-fluoro-4-(methylsulfonamidomethyl)phenylcarbamate

HRID 1428740Notes

Reaction equation

HRID 1428740 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])=[C:4]([F:14])[CH:3]=1.[C:15]1([O:21][C:22](Cl)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1C=CC=CC=1>O1CCCC1.C(#N)C.C(OCC)(=O)C>[F:14][C:4]1[CH:3]=[C:2]([NH:1][C:22](=[O:23])[O:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][C:5]=1[CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9]

Participants

7

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 86679367N-(4-amino-2-fluorobenzyl)methanesulfonamide

Product 1

HCID 86679368Phenyl 3-fluoro-4-(methylsulfonamidomethyl)phenylcarbamateYield 85%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-(4-amino-2-fluorobenzyl)methanesulfonamide (190 mg, 0.871 mmol) in tetrahydrofuran and acetonitrile as co-solvent were added phenylchloroformate (0.115 ml, 0.914 mmol) and pyridine (0.084 ml, 1.045 mmol). The reaction mixture was stirred for 1 h at room temperature. The mixture dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate was removed in vacuo. The crude was purified by column chromatography. Phenyl 3-fluoro-4-(methylsulfonamidomethyl)phenylcarbamate (250 mg) was obtained as 85% yield.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was removed in vacuo
  5. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-ecfd50b90de44a79ae2b49c635cca9b9
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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