Methyl Thioglycolate → HCID 18796972, compound

HRID 442775Notes

Reaction equation

HRID 442775 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][N:3]=1.[C:12]([O:16][CH3:17])(=[O:15])[CH2:13][SH:14].CC([O-])(C)C.[K+].C1COCC1>CN(C=O)C>[NH2:9][C:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][C:6]=2[O:10][CH3:11])[S:14][C:13]=1[C:12]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 14709302-Chloro-4-methoxynicotinonitrileHCID 66863523KOtBu THF

Product 1

HCID 18796972HCID 18796972, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-chloro-3-cyano-4-methoxypyridine (2.02 g) and methyl thioglycolate (1.1 mL) in DMF (24 mL) at 5° C. was added a 1.0M solution of KOtBu/THF (14.6 mL). The reaction was stirred 20 min at 5°, then 1 h at RT, quenched in saturated NH4Cl, the solid collected, washed with water and sucked dry. This was recrystallized from EtOAc to give 0.89 g of the title compound.

Workup

  1. custom1 h at RT, quenched in saturated NH4Cl
  2. customthe solid collected
  3. washwashed with water
  4. customsucked dry
  5. customThis was recrystallized from EtOAc

Sources & evidence

ORD record
ord-f0f6d87596314cf6afda2f0356b92349
Source dataset
uspto-grants-1999_04
Patent number
US05891882

Reaction notes

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