Dimethylformamide → 5-(2-Methoxy-ethyl)-4-methyl-thiophene-2-sulfonyl chloride

HRID 1696732Notes

Reaction equation

HRID 1696732 reaction equation
[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].CN(C=O)C.[CH3:11][O:12][CH2:13][CH2:14][C:15]1[S:16][CH:17]=[CH:18][C:19]=1[CH3:20]>>[CH3:11][O:12][CH2:13][CH2:14][C:15]1[S:16][C:17]([S:1]([Cl:5])(=[O:3])=[O:2])=[CH:18][C:19]=1[CH3:20]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24648Sulfuryl chlorideHCID 668571532-(2-Methoxy-ethyl)-3-methyl-thiophene

Product 1

HCID 866195455-(2-Methoxy-ethyl)-4-methyl-thiophene-2-sulfonyl chloride

Conditions

Temperature
100 °C

Procedure

Sulfuryl chloride (0.26 g, 1.9 mmol) was added drop wise to a stirred solution of dry DMF (0.14 ml, 1.9 mmol) at 0° C. under an argon atmosphere resulting in the formation of a white solid. After 15 min, 2-(2-methoxy-ethyl)-3-methyl-thiophene (250 mg, 1.6 mmol) was added and the mixture was warmed to 100° C. and the melt was further stirred for 45 min. Crushed ice was added and the reaction mixture was extracted with ethyl acetate (2×) and the combined organic extracts were washed with water, brine, dried (magnesium sulfate. dihydrate), filtered and concentrated under reduced pressure. The crude solid was purified over silica gel (ethyl acetate/ n-heptane): light yellow oil, 220 mg, GC-MS (EI): M=254.

Workup

  1. customresulting in the formation of a white solid
  2. additionCrushed ice was added
  3. extractionthe reaction mixture was extracted with ethyl acetate (2×)
  4. washthe combined organic extracts were washed with water, brine
  5. dry with materialdried (magnesium sulfate. dihydrate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude solid was purified over silica gel (ethyl acetate/ n-heptane)

Sources & evidence

ORD record
ord-b0b27ca882c74ac9b717db4833529cb4
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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