2-Methylpyridine → 1,1'-{Disulfanediylbis[ethane-2,1-diylimino(4-oxobutane-4,1-diyl)]}bis(2-methyl-pyridinium)dichloride

HRID 2237339Notes

Reaction equation

[S:1]([CH2:12][CH2:13][NH:14][C:15](=[O:20])[CH2:16][CH2:17][CH2:18]Cl)[S:2][CH2:3][CH2:4][NH:5][C:6](=[O:11])[CH2:7][CH2:8][CH2:9][Cl:10].[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O.C(#N)C>[Cl-:10].[Cl-:10].[S:1]([CH2:12][CH2:13][NH:14][C:15](=[O:20])[CH2:16][CH2:17][CH2:18][N+:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27])[S:2][CH2:3][CH2:4][NH:5][C:6](=[O:11])[CH2:7][CH2:8][CH2:9][N+:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27]

Participants

Conditions

Temperature: 50 °C

Procedure

1.13 g of N,N′-(disulfanediyldiethane-2,1-diyl)bis(4-chlorobutanamide) was dispersed in 0.5 mL of N-methylpyrrolidinone and 2.5 mL acetonitrile and heated at 50° C. 0.71 mL of picoline was added and the reaction mixture was stirred for 5 days at 50° C. A few milligrams of cesium carbonate and additional 0.35 mL of 2-picoline were added. After one day at 65° C., the reaction mixture was poured in 50 mL acetonitrile. The resulting gum was washed several times with ethyl acetate, solubilized in ethanol, filtered and dried under vacuum. 0.95 g of a beige solid were obtained.

Workup

waitAfter one day at 65° C.
washThe resulting gum was washed several times with ethyl acetate
filtrationfiltered
customdried under vacuum

Sources & evidence

ORD record: ord-a773d9dad514481f9ac1c0dc23982102
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07717964B2

Reaction notes

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