Ethanol → HCID 86739881, compound

HRID 280598Notes

Reaction equation

HRID 280598 reaction equation
[CH3:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]([OH:13])=[S:12])[CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1.P(Cl)(Cl)(Cl)=O.[CH2:19](O)[CH3:20]>>[CH2:19]([O:13][C:11]([C:9]1[CH:8]=[CH:7][C:4]2[S:5][CH:6]=[C:2]([CH3:1])[C:3]=2[CH:10]=1)=[S:12])[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 24813Phosphorus oxychlorideHCID 178431819HCID 178431819, compound

Product 1

HCID 86739881HCID 86739881, compound

Procedure

A mixture of 3-methylthiobenzo[b]thiophene-5-carboxylic acid (5.62 g) and phosphorous oxychloride (2 ml) in ethanol (200 ml) was heated under reflux for 18 hours and then evaporated. The residue was dissolved in ether and the solution was washed with sodium bicarbonate solution, and water and dried (Na2SO4). Evaporation of the solvent gave a solid which was crystallised from ethanol to give 3-methylthiobenzo[b]thiophene-5-carboxylic acid ethyl ester (5.84 g), m.p. 67°-69°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customevaporated
  4. dissolutionThe residue was dissolved in ether
  5. washthe solution was washed with sodium bicarbonate solution, and water
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent
  8. customgave a solid which
  9. customwas crystallised from ethanol

Sources & evidence

ORD record
ord-8c4deb9a357948a9a796a0767ccd556a
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

Loading…