Methyl iodide → HCID 19967386, compound

HRID 976647Notes

Reaction equation

HRID 976647 reaction equation
[H-].[Na+].[CH2:3]([O:10][NH:11][C:12]([N:14]([CH3:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H].[CH3:24]I>CN(C)C=O>[CH2:3]([O:10][N:11]([CH3:24])[C:12]([N:14]([CH3:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19967416HCID 19967416, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19967386HCID 19967386, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, a flask was charged with sodium hydride (0.29 g 60% NaH in mineral oil, 7.3 mmole). The mineral oil was washed from the sodium hydride using several portions of hexanes. N,N-Dimethylformamide (60 mL) was added followed by the slow addition of a solution of 1-benzyloxy-3-methyl-3-phenylurea (1.69 g, 6.6 mmole) in N,N-dimethylformamide (40 mL). Hydrogen evolution was observed. After about 30 minutes methyl iodide (480 μL) was added then the reaction was stirred at ambient temperature for about 1.5 hours. The reaction was quenched with water (about 65 mL). The aqueous layer was salted then extracted with diethyl ether (4×80 mL). The extracts were combined, dried over magnesium sulfate then concentrated to provide crude product as an oil. The crude product was purified by silica gel chromatography (5:1 hexanes:ethyl acetate) to provide 1.54 g of 1-benzyloxy-1,3-dimethyl-3-phenylurea.

Workup

  1. washThe mineral oil was washed from the sodium hydride using several portions of hexanes
  2. additionN,N-Dimethylformamide (60 mL) was added
  3. customThe reaction was quenched with water (about 65 mL)
  4. extractionThe aqueous layer was salted then extracted with diethyl ether (4×80 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationthen concentrated
  7. customto provide crude product as an oil
  8. customThe crude product was purified by silica gel chromatography (5:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-0fa17c37ae2240caa827eea08000c579
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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