Water → HCID 22320529, compound

HRID 497897Notes

Reaction equation

HRID 497897 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[C:8]1[CH2:21][CH2:22][CH3:23].[CH3:24][S-:25].[Na+].O>CN(C)C=O>[CH3:24][S:25][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[C:8]1[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 22320419HCID 22320419, compound

Product 1

HCID 22320529HCID 22320529, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 1-(5-chloropentyl)-2-propyl-1H-imidazo[4,5-c]quinoline-4-amine (2.5 g, 7.56 mmol) in anhydrous N,N-dimethylformamide (38 mL) was heated to 80° C. to provide a light yellow solution. Sodium thiomethoxide (0.67 g of 95%, 9.07 mmol) was added in a single portion and heating was continued for 110 minutes. The resulting light brown suspension was poured into water (300 mL) with rapid stirring. A white solid precipitated. After the suspension had cooled to ambient temperature, several scoops of solid sodium carbonate were added. The suspension was chilled in an ice water bath with stirring for 1 hour. The solid was isolated by filtration, washed with cold water and then dried to provide 2.3 g of 1-[5-(methylthio)pentyl]-2-propyl-1H-imidazo[4,5-c]quinoline-4-amine as a white powder.

Workup

  1. customto provide a light yellow solution
  2. temperatureheating
  3. customA white solid precipitated
  4. temperatureAfter the suspension had cooled to ambient temperature
  5. additionseveral scoops of solid sodium carbonate were added
  6. temperatureThe suspension was chilled in an ice water bath
  7. customThe solid was isolated by filtration
  8. washwashed with cold water
  9. customdried

Sources & evidence

ORD record
ord-c4239c9cfaa2463eafcb40485c639334
Source dataset
uspto-grants-2005_09
Patent number
US06949649B2

Reaction notes

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