Methyl Thioglycolate → HCID 18796915, compound

HRID 442772Notes

Reaction equation

HRID 442772 reaction equation
Cl[C:2]1[C:3]([C:10]#[N:11])=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[C:12]([O:16][CH3:17])(=[O:15])[CH2:13][SH:14].C[O-].[Na+]>CN(C=O)C>[NH2:11][C:10]1[C:3]2=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=[C:2]2[S:14][C:13]=1[C:12]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 10942334Sodium Methoxide2×HCID 187968643-Chloro-5-methoxypicolinonitrile

Product 1

HCID 18796915HCID 18796915, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 27B (0.168 g, 1.0 mmol) and methyl thioglycolate (0.09 mL, 1.0 mmol) were combined in DMF (2 mL). To the solution was added 0.054 g NaOMe. After 1 hr, and additional 0.07 g NaOMe was added. After an additional 1 hr, the reaction was quenched in sat aq. NH4Cl and extracted with ethyl acetate. The organic phase was dried (MgSO4), and evaporated to yield 0.17 g of the title compound: 1H NMR (300 MHz, CDCl3) δ 3.90 (s, 3H), 3.93 (s, 3H), 6.15 (br s, 2H), 7.44 (d, 1H), 8.36 (d, 1H).

Workup

  1. waitAfter an additional 1 hr
  2. customthe reaction was quenched in sat aq. NH4Cl
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-2bac50943cc445fdb5bb6348a670d2e4
Source dataset
uspto-grants-1999_04
Patent number
US05891882

Reaction notes

Loading…