Benzyl Chloride → HCID 13958467, compound

HRID 255547Notes

Reaction equation

HRID 255547 reaction equation
[CH2:1]([N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=[C:6]1[SH:18])[CH:2]([CH3:4])[CH3:3].C[O-].[Na+].[CH2:22]([Cl:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO>[ClH:29].[CH2:22]([S:18][C:6]1[N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 10942334Sodium MethoxideHCID 178448729HCID 178448729, compound

Product 1

HCID 13958467HCID 13958467, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 4.4 g (0.071 mole) of 1-isobutyl-2-mercapto-1H-imidazo[4,5-c]quinoline (from Example 164, Part B below) in 45 ml of methanol and was added 4.1 g (0.0188) of 25% sodium methoxide in methanol, then 2.4 g (0.0188 mole) of benzyl chloride. The solution was heated at reflux for 0.5 hour, then evaporated. Water was added to the residue, and the mixture was extracted with dichloromethane. The extracts were dried over sodium chloride, and then evaporated. The residue was dissolved in diethyl ether, and the solution was saturated with hydrogen chloride. The precipitate was separated by filtration, washed with ether and recrystallized from a mixture of ethanol and diethyl ether to provide 2-benzylthio-1-isobutyl-1H-imidazo[4,5-c]quinoline hydrochloride, m.p. 205°-207° C. Analysis: Calculated for C21H21N3S.HCl: %C, 65.7; %H, 5.8; %N, 10.9; Found: %C, 65.4; %H, 5.6; %N, 10.9.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 0.5 hour
  3. customevaporated
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with dichloromethane
  6. dry with materialThe extracts were dried over sodium chloride
  7. customevaporated
  8. dissolutionThe residue was dissolved in diethyl ether
  9. customThe precipitate was separated by filtration
  10. washwashed with ether
  11. customrecrystallized from a mixture of ethanol and diethyl ether

Sources & evidence

ORD record
ord-697a36c5cde4410ba494214db2a2374c
Source dataset
uspto-grants-1987_10
Patent number
US04698348

Reaction notes

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