Methyl iodide → HCID 20200507, compound

HRID 979517Notes

Reaction equation

HRID 979517 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[CH:5][C:6]2[CH:7]=[C:8]3[NH:15][C:14](=[S:16])[NH:13][C:9]3=[N:10][C:11]=2[CH:12]=1.[OH-].[Na+].[CH3:21]I>CO>[CH3:21][S:16][C:14]1[NH:15][C:8]2[C:9]([N:13]=1)=[N:10][C:11]1[CH:12]=[C:3]([C:2]([F:17])([F:1])[F:18])[CH:4]=[CH:5][C:6]=1[CH:7]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 13937025HCID 13937025, compound

Product 1

HCID 20200507HCID 20200507, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 1,3-dihydro-6-(trifluoromethyl)-2H-imdazo[4,5-b]quinolin-2-thione (0.53 g, 2 mmol) in methanol (5 mL) was treated with 50% aqueous sodium hydroxide (0.18 g) to afford a solution which was cooled in an ice bath. Methyl iodide (0.3 g, 0.13 mL, 2.1 mmol) was added and the mixture stirred for 90 minutes before being filtered. The solid was washed with methanol and dried in air to give 2-(methylthio)-6-(trifluoromethyl)-1H-imidazo[4,5-b]quinoline (0.34 g, 61%), m.p. >270° C.

Workup

  1. customto afford a solution which
  2. temperaturewas cooled in an ice bath
  3. filtrationbefore being filtered
  4. washThe solid was washed with methanol
  5. customdried in air

Sources & evidence

ORD record
ord-9f969aeba2464b8489498af5dd99fe81
Source dataset
uspto-grants-1987_05
Patent number
US04668686

Reaction notes

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