Methyl iodide → 2-(Methylthio)thiazolo[4,5-c]quinoline

HRID 858010Notes

Reaction equation

HRID 858010 reaction equation
[CH3:1][O-].[Na+].CI.[S:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:8]=[C:7]1[SH:19]>CO>[CH3:1][S:19][C:7]1[S:6][C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 178527812HCID 178527812, compound

Product 1

HCID 226483122-(Methylthio)thiazolo[4,5-c]quinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (15.8 mL of 25% in methanol, 69 mmol) and methyl iodide (3.9 mL, 63 mmol) were added to a solution of thiazolo[4,5-c]quinoline-2-thiol (13.65 g, 63 mmol) in methanol (160 mL). The reaction mixture was heated on a steam bath for 1 hour. The solvent was removed under vacuum. The resulting light green-yellow solid was slurried with water, isolated by filtration, and washed with water to provide 9.8 g of crude product. A portion (1 g) was recrystallized from methanol to provide 2-(methylthio)thiazolo[4,5-c]quinoline as a solid, m.p. 116–119° C. Analysis: Calculated for C11H8N2S2: % C, 56.87; % H, 3.47; % N, 12.06; Found: % C, 57.09; % H, 3.57; % N, 12.04.

Workup

  1. temperatureThe reaction mixture was heated on a steam bath for 1 hour
  2. customThe solvent was removed under vacuum
  3. customisolated by filtration
  4. washwashed with water
  5. customto provide 9.8 g of crude product
  6. customA portion (1 g) was recrystallized from methanol

Sources & evidence

ORD record
ord-ced5187b0b964054adeccae0c4440c63
Source dataset
uspto-grants-2006_12
Patent number
US07148232B2

Reaction notes

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