Sulfuryl chloride → HCID 20558380, compound

HRID 1660330Notes

Reaction equation

HRID 1660330 reaction equation
[S:1]1[CH2:5][CH2:4][C:3](=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:7]([O:9][CH3:10])=[O:8])[CH2:2]1.S(Cl)(Cl)(=O)=O>C1(C)C=CC=CC=1>[S:1]1[CH:5]=[CH:4][C:3](=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:7]([O:9][CH3:10])=[O:8])[CH2:2]1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 13308342HCID 13308342, compound

Product 1

HCID 20558380HCID 20558380, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 0.50 g (2.31 mol) of dimethyl 2-(3-tetrahydrothienylidene)malonate in 10 ml of toluene was treated with 0.32 g (2.35 mmole) of sulfuryl chloride in 1 ml of toluene under nitrogen at ice bath temperature. The mixture turned dark, and starting material could not be observed by tlc after 5 min. Nitrogen was bubbled through the solution for 5 min., and the dark color faded. Pyridine (1 ml) was added. After 15 min. at room temperature, the solution was worked up as in Example 1 and molecular distillation gave 0.45 g (93%) of dimethyl 2-(3-thienylidene)malonate, containing minor impurities by glc (SE-30, 200° ).

Workup

  1. customtlc after 5 min
  2. customNitrogen was bubbled through the solution for 5 min.
  3. additionPyridine (1 ml) was added
  4. distillationthe solution was worked up as in Example 1 and molecular distillation

Sources & evidence

ORD record
ord-316761c50da34482ae67e0d7925701ad
Source dataset
uspto-grants-1981_12
Patent number
US04307239

Reaction notes

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