Sodium methanethiolate → HCID 19592663, compound

HRID 613465

Reaction equation

HRID 613465 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8](Br)=[CH:7]2.[CH3:13][S-:14].[Na+]>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([S:14][CH3:13])=[CH:7]2

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 151125453-Bromoquinolin-8-amine

Product 1

HCID 19592663HCID 19592663, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8-amino-3-bromoquinoline (200 mg) and sodium thiomethoxide (109 mg) in N,N-dimethylformamide (2 ml) was stirred at ambient temperature for 2 days. After diluted with ethyl acetate, the resulting mixture was washed with water and brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by chromatography on silica gel (n-hexane-ethyl acetate) to give 8-amino-3-methylthioquinoline (113 mg) as an oil.

Workup

  1. washthe resulting mixture was washed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-802c2d8881664f5886a4efecce353081
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Linked notes

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