Methanesulfonate → 2,2'-Thiodipyridine

HRID 1088028Notes

Reaction equation

HRID 1088028 reaction equation
[S:1]([O-])(=O)(=O)[CH3:2].S[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1>C(#N)C>[N:10]1[CH:11]=[CH:12][CH:7]=[CH:8][C:9]=1[S:1][C:2]1[CH:12]=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 85257MethanesulfonateHCID 178418431pyridine-4-thiol

Product 1

HCID 5211142,2'-ThiodipyridineYield 22.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

This product (4) is treated with 4-mercaptopyridine (129 mg; 1.4 equivalents) in acetonitrile (2 ml) at 0° C. for 1 hour to give pyridylthioylide (7) as in Example F-3. This is heated in toluene (35 ml) at 110° C. for 1 hour as in Example E-8 to give 6α-(1-hydroxyethyl)-1-ethyl-2-(4-pyridylthio)methyl-1-carbapen-2-em-3-carboxylic acid p-methoxybenzyl ester (b) {86 mg; IR (CHCl3)ν: 3680, 3604, 1772, 1712, 1612, 1586 cm-1, Yield: 22.8%} and two other products.

Sources & evidence

ORD record
ord-6b79ee781f3d4862bebc9bd3645401c8
Source dataset
uspto-grants-1990_10
Patent number
US04960879

Reaction notes

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