Sodium 2-propanethiolate → HCID 67203149, compound

HRID 547300Notes

Reaction equation

HRID 547300 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[C:12]([NH2:21])[C:11]=2[N:10]=[C:9]1[CH2:22][CH2:23][CH3:24].[CH3:25][CH:26]([S-:28])[CH3:27].[Na+]>CN(C=O)C>[CH3:25][CH:26]([S:28][CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[C:12]([NH2:21])[C:11]=2[N:10]=[C:9]1[CH2:22][CH2:23][CH3:24])[CH3:27]

Participants

4

Reactant 2

HCID 3470666Sodium 2-propanethiolateHCID 67203500HCID 67203500, compound

Product 1

HCID 67203149HCID 67203149, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Nitrogen was bubbled through a solution of 1-[2-(3-chloropropoxy)ethyl]-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (2.50 g, 7.21 mmol) in DMF (25 mL) for 5 minutes. Sodium 2-propanethiolate (0.85 g 8.65 mmol) was added and the reaction mixture was stirred under a nitrogen atmosphere at ambient temperature. After 16 hours analysis by HPLC indicated that 50% of the starting material had been consumed. Additional sodium 2-propanethiolate (0.6 g) was added followed by a second addition (0.25 g) 2.5 hours later. After a total of 21 hours the reaction mixture was poured into water (250 mL) with rapid stirring. The resulting tan precipitate was isolated by filtration to provide 2.34 g of 1-(2-{3-[(1-methylethyl)thio]propoxy}ethyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine.

Workup

  1. customhad been consumed
  2. additionAdditional sodium 2-propanethiolate (0.6 g) was added
  3. additionfollowed by a second addition (0.25 g) 2.5 hours later
  4. additionAfter a total of 21 hours the reaction mixture was poured into water (250 mL) with rapid stirring
  5. customThe resulting tan precipitate was isolated by filtration

Sources & evidence

ORD record
ord-5bf0f1f7373743b7aa7f22098d55e687
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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