Ammonium thiocyanate → Methyl 3-Bromo-3-Thiocyanoacrylate

HRID 128565

Reaction equation

HRID 128565 reaction equation
[S-:1][C:2]#[N:3].[NH4+].[Br:5][C:6]#[C:7][C:8]([O:10][CH3:11])=[O:9]>S(=O)(=O)(O)O>[Br:5][C:6]([S:1][C:2]#[N:3])=[CH:7][C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 15666Ammonium thiocyanateHCID 294619Methyl 3-bromoprop-2-ynoate

Product 1

HCID 54348499Methyl 3-Bromo-3-Thiocyanoacrylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred solution of ammonium thiocyanate (3.06 g., 0.04 mole) in 2M aqueous sulfuric acid (20 ml) at 0° C., methyl 3-bromopropiolate (3.26 g., 0.02 mole) was added dropwise, neat, over 5 minutes. After keeping the temperature at 0° C. for 1 hour, the mixture, consisting of a solid precipitate in the aqueous solution, was extracted with ether which was washed with water, dried (MgSO4), and concentrated. The residual solid was suspended in hexane and removed by filtration, yielding 2.4 g. of product. The solid recrystallized from ethanol as yellowish microcrystals; mp 139°-142.5° C.; IR (KBr) 2170, 1680 cm-1.

Workup

  1. customat 0° C.
  2. customfor 1 hour
  3. extractionwas extracted with ether which
  4. washwas washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customremoved by filtration
  8. customyielding 2.4 g
  9. customThe solid recrystallized from ethanol as yellowish microcrystals

Sources & evidence

ORD record
ord-ea6c9949fb164a7596e52014184b1aec
Source dataset
uspto-grants-1995_11
Patent number
US05464832

Linked notes

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