Methanethiol → HCID 10131763, compound

HRID 991899Notes

Reaction equation

HRID 991899 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:16])[C:7]=2[N:17]=1.[CH3:25][SH:26].C[O-].[Na+]>CO>[CH3:25][S:26][CH2:3][C:4]1[N:5]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:16])[C:7]=2[N:17]=1

Participants

5

Reactant 3

HCID 878MethanethiolHCID 10942334Sodium MethoxideHCID 69878366HCID 69878366, compound

Product 1

HCID 10131763HCID 10131763, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloromethyl-1-phenylmethyl-1H-imidazo-[4,5-c]quinolin-4-amine hydrochloride (Example 28, prepared from 2.11 g of the alcohol) was added to a solution of methanethiol (1.33 g; 0.028 mol) and sodium methoxide (1.5 g; 0.028 mol) in methanol. The solid dissolved upon addition and a cream colored solid precipitated during addition. After stirring at room temperature for several hours the mixture was diluted with water. The solid was filtered from the mixture, washed with water, and dried. A crude yield of 2.3 g was obtained. The product was purified by silica gel flash chromatography (10% methanol in ethyl acetate eluent) and recrystallized from methanol/dichloromethane to give a cream colored solid, m.p. 217-219° C. Analysis: Calculated: C, 68.2; H, 5.4; N, 16.8. Found: C, 67.5; H, 5.3; N, 16.6.

Workup

  1. dissolutionThe solid dissolved upon addition
  2. customprecipitated during addition
  3. additionwas diluted with water
  4. filtrationThe solid was filtered from the mixture
  5. washwashed with water
  6. customdried
  7. customA crude yield of 2.3 g was obtained
  8. customThe product was purified by silica gel flash chromatography (10% methanol in ethyl acetate eluent)
  9. customrecrystallized from methanol/dichloromethane
  10. customto give a cream colored solid, m.p. 217-219° C

Sources & evidence

ORD record
ord-b884105b2f3e489dacdf2ec93eb3f6e2
Source dataset
uspto-grants-2002_10
Patent number
US06465654B2

Reaction notes

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