Methyl Thioglycolate → HCID 18322377, compound

HRID 1698886Notes

Reaction equation

HRID 1698886 reaction equation
C[O-].[Na+].[C:4]([O:8][CH3:9])(=[O:7])[CH2:5][SH:6].Cl[C:11]([CH:15]([CH3:17])[CH3:16])=[CH:12][C:13]#[N:14]>CO>[NH2:14][C:13]1[CH:12]=[C:11]([CH:15]([CH3:17])[CH3:16])[S:6][C:5]=1[C:4]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 10942334Sodium MethoxideHCID 53838025HCID 53838025, compound

Product 1

HCID 18322377HCID 18322377, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of NaOMe (14 g) in MeOH (1 L) was added methyl thioglycolate (22.3 mL). The mixture was stirred for 5 min, then a solution of 3-chloro-4-methyl-2-pentenenitrile (32.4 g) in MeOH (200 mL) was added and the solution was heated at the reflux temp. for 90 min. After cooling to 20° C., the mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc, washed with a 1N HCl solution, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (EtOAc/hexane) to yield methyl 3-amino-5-isopropylthiophene-2-carboxylate (8.0 g, 16%).

Workup

  1. temperaturethe solution was heated at the reflux temp
  2. waitfor 90 min
  3. concentrationthe mixture was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with a 1N HCl solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-ce7be3d7156344b19641e16ade6a71de
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Reaction notes

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