Sodium hydride → 1553712-23-4

HRID 2278935Notes

Reaction equation

HRID 2278935 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][CH2:8][CH2:9][CH2:10][O:11][CH3:12])=[O:6].[H-].[Na+].[NH4+].[Cl-]>C1COCC1.[Cl-].[Na+].O>[CH3:12][O:11][CH2:10][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 90427351HCID 90427351, compound

Product 1

HCID 904281761553712-23-4Yield 88%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A 0° C. solution of 1-(2-chloroethyl)-3-(3-methoxypropyl)urea (0.300 g, 1.541 mmol) in THF (8 mL), under Ar, was treated with NaH (60% in mineral oil, 0.154 g, 3.85 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 10 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-(3-methoxypropyl)imidazolidin-2-one (214 mg, 88%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 6.21 (s, 1 H), 3.31-3.24 (m, 4 H), 3.21-3.15 (m, 5 H), 3.06-3.01 (m, 2 H), 1.66-1.58 (m, 2 H); MS (ESI) m/z: 159.1 (M+H+).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. additiontreated slowly with satd
  3. stirringstirred for 10 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-6c54a8c236894f10a423ca269feb6464
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

Loading…