Pyridine → Phenyl 3-cyano-4-(ethylsulfonyl)phenylcarbamate

HRID 735558Notes

Reaction equation

HRID 735558 reaction equation
[C:1]1([O:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[C:16]([CH:19]=1)[C:17]#[N:18].N1C=CC=CC=1>C(Cl)Cl>[C:17]([C:16]1[CH:19]=[C:12]([NH:11][C:8](=[O:9])[O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:13]=[CH:14][C:15]=1[S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])#[N:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 598380375-Amino-2-(ethanesulfonyl)benzonitrile

Product 1

HCID 68818495Phenyl 3-cyano-4-(ethylsulfonyl)phenylcarbamateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenylchloroformate (0.63 mL, 5 mmol) was added dropwise to a solution of 6B in methylene chloride (10 mL) and pyridine (0.60 mL, 7.1 mmol) at 0° C. After stirring for 1 h, the reaction mixture was partitioned between 1.0 M HCl (150 mL) and EtOAc (150 mL). The layers were separated and the organic phase was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes) to yield 25A (1.34 g, 85%) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 1.32 (t, J=7.45 Hz, 3 H) 3.36 (q, J=7.33 Hz, 2 H) 7.14-7.21 (m, J=7.58 Hz, 2 H) 7.26-7.31 (m, J=7.45, 7.45 Hz, 1 H) 7.37-7.45 (m, J=7.83, 7.83 Hz, 2 H) 7.66 (bs, 1 H) 7.83 (dd, J=8.72, 2.15 Hz, 1 H).

Workup

  1. customthe reaction mixture was partitioned between 1.0 M HCl (150 mL) and EtOAc (150 mL)
  2. customThe layers were separated
  3. washthe organic phase was washed with saturated NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f797af9a6dd54bbcb04b5416b86c9a92
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

Loading…