Dimethylacetamide → 5-(Tetradecylsulfanyl)thiophene-2-carboxylic acid

HRID 596651Notes

Reaction equation

HRID 596651 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH2:10]([SH:24])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].CC(N(C)C)=O.C[O-].[Na+]>CO>[CH2:10]([S:24][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 31374DimethylacetamideHCID 646771-TetradecanethiolHCID 3491155-Bromothiophene-2-carboxylic acidHCID 10942334Sodium Methoxide

Product 1

HCID 123615115-(Tetradecylsulfanyl)thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 18.6 g (0.090 mole) of 5-bromo-2-thiophenecarboxylic acid, 25.0 g (0.109 mole) of 1-tetradecanethiol and 500 ml of dried dimethyl acetamide is stirred at room temperature after which 10.8 g (0.200 mole) of sodium methoxide is added. The mixture is heated and the methanol formed is allowed to distill off. The mixture is refluxed for 24 hours after which the mixture is cooled and poured into a water-ice mixture, acidified with 10% aqueous hydrochloric acid, filtered, and the precipitate washed with water and dried. The solid obtained is crystallized from the methanol then recrystallized from hexane to give 5-(tetradecylthio)-2 -thiophene carboxylic acid, M.P. 106°-108° C.

Workup

  1. additionis added
  2. temperatureThe mixture is heated
  3. distillationto distill off
  4. temperatureThe mixture is refluxed for 24 hours after which the mixture
  5. temperatureis cooled
  6. additionpoured into a water-ice mixture
  7. filtrationfiltered
  8. washthe precipitate washed with water
  9. customdried
  10. customThe solid obtained
  11. customis crystallized from the methanol
  12. customthen recrystallized from hexane

Sources & evidence

ORD record
ord-37694ceb4bc2473ea45a686ace160e65
Source dataset
uspto-grants-1977_03
Patent number
US04011333

Reaction notes

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