Benzyl mercaptan → Pyridine, 3-chloro-2-[(phenylmethyl)thio]-

HRID 1154532Notes

Reaction equation

[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][N:11]=1>CN(C)C=O>[Cl:16][C:15]1[C:10]([S:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 70 °C

Procedure

42.0 Grams (0.338 mole) of benzyl mercaptan were dissolved in 350 ml dimethylformamide which had been dried over molecular sieves. The solution was placed under a nitrogen atmosphere and 16.2 grams (0.338 mole) of a 50 percent dispersion of sodium hydride was slowly added. Stirring was continued until hydrogen gas evolution stopped. Thereupon, the resulting solution was added slowly, again with stirring, to a solution of 50.0 grams (0.338 mole) of 2,3-dichloropyridine in 200 ml dry dimethylformamide. The mixture was heated at 70° C. for 4 hours.

Workup

customhad been dried over molecular sieves
addition16.2 grams (0.338 mole) of a 50 percent dispersion of sodium hydride was slowly added
additionThereupon, the resulting solution was added slowly

Sources & evidence

ORD record: ord-2030a9931dca4ed69dadfdcaaaa2cf3a
Source dataset: uspto-grants-1984_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04490380

Reaction notes

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