2-(Benzenesulfonyl)-3-phenyloxaziridine → 6-Amino-4-furan-2-yl-2-methanesulfinyl-nicotinonitrile

HRID 1356067Notes

Reaction equation

HRID 1356067 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[C:5]([C:6]#[N:7])=[C:4]([S:15][CH3:16])[N:3]=1.C1(C2[O:25]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>ClCCl>[NH2:1][C:2]1[CH:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[C:5]([C:6]#[N:7])=[C:4]([S:15]([CH3:16])=[O:25])[N:3]=1

Participants

4

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 185075176-Amino-4-furan-2-yl-2-methylsulfanyl-nicotinonitrile

Product 1

HCID 185075486-Amino-4-furan-2-yl-2-methanesulfinyl-nicotinonitrileYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 600 mg (2.59 mmol) 6-amino-4-furan-2-yl-2-methylsulfanyl-nicotinonitrile in 10 ml dichloromethane was added 1,36 g (5.19 mmol) 3-phenyl-2-(phenylsulfonyl)oxaziridine and stirring continued for 16 hours at room temperature. The resulting crystals were collected by filtration and washed with dichloromethane to afford 500 mg (78%) 6-amino-4-furan-2-yl-2-methanesulfinyl-nicotinonitrile as a white crystalline solid. EI-MS m/e (%): 247 (M+, 26), 230 (12), 201 (100), 184 (24), 172 (27), 156 (28), 129 (24), 102 (13).

Workup

  1. filtrationThe resulting crystals were collected by filtration
  2. washwashed with dichloromethane

Sources & evidence

ORD record
ord-7127d9bb90034dbcaa1ec26601fe8c10
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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