Sodium hydride → HCID 54174918, compound

HRID 2278933Notes

Reaction equation

HRID 2278933 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][CH2:8][CH2:9][O:10][CH3:11])=[O:6].[H-].[Na+].[NH4+].[Cl-]>C1COCC1.[Cl-].[Na+].O>[CH3:11][O:10][CH2:9][CH2:8][N:7]1[CH2:2][CH2:3][NH:4][C:5]1=[O:6]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 90426063HCID 90426063, compound

Product 1

HCID 54174918HCID 54174918, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A −20° C. solution of 1-(2-chloroethyl)-3-(2-methoxyethyl)urea (0.300 g, 1.661 mmol) in THF (8.3 mL), under Ar, was treated with NaH (60% in mineral oil, 0.166 g, 4.15 mmol) allowed to warm to RT and stirred. The mixture was cooled to 0° C., treated slowly with satd. NH4Cl, then brine, warmed to RT and stirred for 20 min. The layers were separated, the aqueous layer extracted with EtOAc (2×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 1-(2-methoxyethyl)imidazolidin-2-one (220 mg, 92%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 6.26 (s, 1 H), 3.39-3.31 (m, 4 H), 3.22 (s, 3 H), 3.20-3.14 (m, 4 H); MS (ESI) m/z: 145.1 (M+H+).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. additiontreated slowly with satd
  3. stirringstirred for 20 min
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted with EtOAc (2×)
  6. dry with materialthe combined organics were dried over Na2SO4
  7. concentrationconcentrated to dryness
  8. custompurified via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-6e5252682e4146388abe8a9aa7a82ea2
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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