Methyl Thioglycolate → HCID 18796904, compound

HRID 1003403Notes

Reaction equation

HRID 1003403 reaction equation
[C:1]([C:3]1[C:8](Cl)=[CH:7][C:6]([Cl:10])=[CH:5][N:4]=1)#[N:2].[C:11]([O:15][CH3:16])(=[O:14])[CH2:12][SH:13].C[O-].[Na+]>C1COCC1>[NH2:2][C:1]1[C:3]2=[N:4][CH:5]=[C:6]([Cl:10])[CH:7]=[C:8]2[S:13][C:12]=1[C:11]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 27696993,5-Dichloro-2-cyanopyridineHCID 10942334Sodium Methoxide2×

Product 1

HCID 18796904HCID 18796904, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 27A (3,46 g, 20 mmol) and methyl thioglycolate (1.8 mL, 20 mmol) were combined in 40 mL THF. To the solution was added 1.08 g NaOMe (20 mmol) After 1.5 h, and additional 1.08 g NaOMe was added, and then after an additional 2 h, the reaction was quenched in 5% aq. NaHCO3 and extracted with diethyl ether. The organic extracts were dried (MgSO4), evaporated, and the product was purified by silica gel colmun chromatography to yield 1.23 g (25%) of the title compound: 1H NMR (300 MHz, CDCl3) δ 3.92 (s, 3H), 6.20 (br s, 2H), 8.04 (d, 1H), 8.54 (d, 1H).

Workup

  1. customthe reaction was quenched in 5% aq. NaHCO3
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. customevaporated
  5. customthe product was purified by silica gel colmun chromatography

Sources & evidence

ORD record
ord-aa3725061f5f4574a74031213941462e
Source dataset
uspto-grants-2000_04
Patent number
US06046207

Reaction notes

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