Methanol → Methyl trans-3-Thiocyanoacrylate

HRID 128564Notes

Reaction equation

HRID 128564 reaction equation
[S-:1][C:2]#[N:3].[NH4+].Cl/[CH:6]=[CH:7]/[C:8]([OH:10])=[O:9].O.[CH3:12]O>S(=O)(=O)(O)O>[S:1](/[CH:6]=[CH:7]/[C:8]([O:10][CH3:12])=[O:9])[C:2]#[N:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 15666Ammonium thiocyanateHCID 638124trans-3-Chloroacrylic acid

Product 1

HCID 12390012Methyl trans-3-Thiocyanoacrylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred solution of ammonium thiocyanate (7.2 g., 0.095 mole) in 4N sulfuric acid solution (50 ml) at 40° C., a solution of trans-3-chloroacrylic acid (10.0 g., 0.095 mole) in 35 ml of methanol was added dropwise within 5 minutes. The mixture was refluxed for 18 hours, cooled and poured into water which was extracted thoroughly with ether. The ether extract was washed with saturated sodium bicarbonate solution and then with water. After drying (MgSO4), the solution was concentrated to give an oil which distilled at 70° C./0.3 mm; yield, 7.2 g.; NMR (CDCl3) 7.3 (d, 1H, J=14.4 cps); 6.35 (d, 1H, J=14.4 cps); 3.8 (s, 3H); IR(KBr) 2180, 1725 cm-1.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. temperaturecooled
  3. extractionwas extracted thoroughly with ether
  4. extractionThe ether extract
  5. washwas washed with saturated sodium bicarbonate solution
  6. dry with materialAfter drying (MgSO4)
  7. concentrationthe solution was concentrated
  8. customto give an oil which
  9. distillationdistilled at 70° C./0.3 mm
  10. customyield

Sources & evidence

ORD record
ord-b774947924214085a465bf72abdf1863
Source dataset
uspto-grants-1995_11
Patent number
US05464832

Reaction notes

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