Hydrogen Sulfide → Thiophene, 2,2'-thiobis-

HRID 596262Notes

Reaction equation

Cl[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[SH2:7]>>[S:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[S:7][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 402Hydrogen Sulfide2×

HCID 72992-Chlorothiophene2×

Product 1

HCID 138094Thiophene, 2,2'-thiobis-

Conditions

Temperature: 560 °C

Procedure

Through a 570-mm long silica tube, 26 mm in diameter, heated to a temperature of 560° C, for 90 minutes are passed 40.0 g (0.34 mole) of 2-chlorothiophene and hydrogen sulphide at a rate of 5.2 litres per hour. The molar ratio of 2-chlorothiophene to hydrogen sulphide is 1:1. The condensate is distilled to give 16 g (48.2 percent by weight) of di(2-thienyl) sulphide boiling at 133°-140° C (5 mm Hg), nD20 = 1.6603, and 6.5 g of the starting 2-chlorothiophene (conversion 84 percent by weight).

Workup

distillationThe condensate is distilled

Sources & evidence

ORD record: ord-3d271068c6d14c168cd3aa3af3ac1456
Source dataset: uspto-grants-1977_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04010210

Reaction notes

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