1,3-Dimethyl-2-imidazolidinone → HCID 12074072, compound

HRID 413925Notes

Reaction equation

HRID 413925 reaction equation
[CH2:1]([O:4][C:5](=[O:26])[CH2:6][CH2:7][C@H:8]([NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)=[O:17])[CH2:9][O:10][CH2:11][O:12][CH2:13][CH3:14])[CH:2]=[CH2:3].CN1CCN(C)C1=O.[CH3:35][O:36][CH2:37]Cl>O1CCCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl-].[NH4+]>[CH2:1]([O:4][C:5](=[O:26])[C@@H:6]([CH2:35][O:36][CH3:37])[CH2:7][C@H:8]([NH:15][C:16]([C:18]1[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[CH:22][CH:23]=1)=[O:17])[CH2:9][O:10][CH2:11][O:12][CH2:13][CH3:14])[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 7864Chloromethyl Methyl EtherHCID 12074071HCID 12074071, compound

Product 1

HCID 12074072HCID 12074072, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolventHCID 2733832Lithium HexamethyldisilazideSolvent

Procedure

To a solution of the compound prepared in Example 4 (1.87 g) and 1,3-dimethyl-2-imidazolidinone (1.7 ml) in tetrahydrofuran (THF; 20 ml), 1M lithium bis(trimethylsilyl)amide (11.4 ml; in THF) was dropped at −78° C., and then the mixture was stirred for 30 minutes at same temperature. Methoxymethyl chloride (1.2 ml) was added to the reaction mixture, and the mixture was stirred for 3 hours. The reaction mixture was diluted with a saturated aqueous solution of ammonium chloride, and warmed to room temperature, and then the solution was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography (toluene:ethyl acetate=2:1) to give the title compound (1.45 g) having the following physical data.

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. extractionthe solution was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (toluene:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-fa6427fb87404029bcad4534c9e75be4
Source dataset
uspto-grants-2003_05
Patent number
US06569899B1

Reaction notes

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