2-Bromo-6-methyl-4-nitropyridine → 2-Bromo-6-methyl-4-(4-nitrophenylsulphanyl)-pyridine

HRID 1603604Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[C:4]([CH3:11])[N:3]=1.[K].[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1)([O-:15])=[O:14]>CN1CCCC1=O>[Br:1][C:2]1[CH:7]=[C:6]([S:22][C:19]2[CH:20]=[CH:21][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=2)[CH:5]=[C:4]([CH3:11])[N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

1.0 g (0.00458 mol) of 2-bromo-6-methyl-4-nitropyridine and 0.885 g (0.00458 mol) of 4-nitrothiophenol potassium salt were dissolved in 10 ml of 1-methyl-pyrrolidone and stirred at 50° C. for 1 hr. The solvent was removed in a high vacuum and the residue was partitioned in water and ethyl acetate. The combined organic phases were washed with sat. sodium chloride solution and dried over MgSO4. After filtration and removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane 1:4 and 1:3 and subsequently dried in a high vacuum. There was obtained 0.945 g (63%) of 2-bromo-6-methyl-4-(4-nitrophenylsulphanyl)-pyridine as yellow crystals; m.p.: 124-126° C.

Workup

customThe solvent was removed in a high vacuum
customthe residue was partitioned in water
washThe combined organic phases were washed with sat. sodium chloride solution
dry with materialdried over MgSO4
filtrationAfter filtration and removal of the solvent the residue
customwas chromatographed on silica gel with ethyl acetate/hexane 1:4 and 1:3
customsubsequently dried in a high vacuum

Sources & evidence

ORD record: ord-ac867f4a942540f18d112f661f40e706
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990105

Reaction notes

Loading…