Chloromethyl ethyl ether → HCID 18995659, compound

HRID 374971Notes

Reaction equation

HRID 374971 reaction equation
[H-].[Na+].[C:3]1([CH2:9][N:10]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:11]2[C:20]3[N:21]=[C:22]([CH3:24])[NH:23][C:19]=3[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:32]([O:34][CH2:35]Cl)[CH3:33]>O1CCCC1.C(OCC)C>[C:26]1([CH2:25][N:10]([CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:11]2[C:20]3[N:21]=[C:22]([CH3:24])[N:23]([CH2:35][O:34][CH2:32][CH3:33])[C:19]=3[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 178432313HCID 178432313, compound

Product 1

HCID 18995659HCID 18995659, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of sodium hydride (0.064 g, 2 mmole) in tetrahydrofuran (15 mL) was cooled in an ice bath. N,N-bis(phenylmethyl)-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (0.5 g, 1.32 mmole) was added and the reaction mixture was allowed to warm to room temperature for 20 minutes. Chloromethyl ethyl ether was added and the reaction mixture was stirred for 30 minutes. The reaction mixture was diluted with diethyl ether, washed twice with water, dried over magnesium sulfate and then concentrated under vacuum. The residue was purified by column chromatography (silica gel eluting with methylene chloride) to provide 0.43 g of N,N-bis(phenylmethyl)-1-ethoxymethyl-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine.

Workup

  1. temperaturewas cooled in an ice bath
  2. washwashed twice with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography (silica gel eluting with methylene chloride)

Sources & evidence

ORD record
ord-c841fb7df6cb486c8e67f70ca2b774ab
Source dataset
uspto-grants-1996_01
Patent number
US05482936

Reaction notes

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