Sodium Hydroxide → HCID 18995653, compound

HRID 374982Notes

Reaction equation

HRID 374982 reaction equation
S(Cl)([Cl:3])=O.[C:5]1([CH2:11][N:12]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:13]2[C:22]3[N:23]=[C:24]([CH2:30][CH2:31][CH2:32]O)[N:25]([CH2:26][O:27][CH2:28][CH3:29])[C:21]=3[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[C:5]1([CH2:11][N:12]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:13]2[C:22]3[N:23]=[C:24]([CH2:30][CH2:31][CH2:32][Cl:3])[N:25]([CH2:26][O:27][CH2:28][CH3:29])[C:21]=3[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 18995664HCID 18995664, compound

Product 1

HCID 18995653HCID 18995653, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Thionyl chloride (5 mL, 68 mmole) was added to N,N-bis(phenylmethyl)-2-(3-hydroxypropyl)-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (1 g, 2.1 mmole) and the reaction mixture was stirred rapidly until thin layer chromatography (silica gel, 10% ethyl acetate in methylene chloride v/v) indicated that the reaction was complete. The reaction mixture was diluted with methylene chloride then neutralized with 10% sodium hydroxide and sodium bicarbonate. The methylene chloride layer was separated, dried over magnesium sulfate and then concentrated under vacuum. The residue was purified by column chromatography (silica gel eluting with 10-30% ethyl acetate in hexanes v/v) to provide 1 g of N,N-bis(phenylmethyl)-2-(3-chloropropyl)-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine.

Workup

  1. customThe methylene chloride layer was separated
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by column chromatography (silica gel eluting with 10-30% ethyl acetate in hexanes v/v)

Sources & evidence

ORD record
ord-3b0ab8116bd8401a9ba0097fec2f8799
Source dataset
uspto-grants-1996_01
Patent number
US05482936

Reaction notes

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