Sodium hydride → HCID 90426481, compound

HRID 2278945Notes

Reaction equation

HRID 2278945 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][CH2:8][CH2:9][C:10]1([O:13][CH3:14])[CH2:12][CH2:11]1)=[O:6].[H-].[Na+]>C1COCC1>[CH3:14][O:13][C:10]1([CH2:9][CH2:8][N:7]2[CH2:2][CH2:3][NH:4][C:5]2=[O:6])[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 90426517HCID 90426517, compound

Product 1

HCID 90426481HCID 90426481, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A −20° C. solution of 1-(2-chloroethyl)-3-(2-(1-methoxycyclopropyl)ethyl)urea (0.429 g, 1.944 mmol) in THF (10 mL), under argon, was treated with NaH (60% in mineral oil, 0.194 g, 4.86 mmol), and the mixture allowed to warm to RT as the cooling bath expired. The mixture was cooled to 0° C., quenched with satd. NH4Cl, warmed to RT, treated with brine, extracted with EtOAc (2×) and the combined organics were dried over MgSO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 1-(2-(1-methoxycyclopropyl)ethyl)imidazolidin-2-one (196 mg, 55%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 6.22 (s, 1 H), 3.32-3.27 (m, 2 H), 3.19-3.17 (m, 2 H), 3.14 (s, 3 H), 3.12-3.11 (m, 2 H), 1.67-1.65 (m, 2 H), 0.63-0.62 (m, 2 H), 0.39-0.38 (m, 2 H); MS (ESI) m/z: 185.1 (M+H+).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customquenched with satd
  3. temperatureNH4Cl, warmed to RT
  4. additiontreated with brine
  5. extractionextracted with EtOAc (2×)
  6. dry with materialthe combined organics were dried over MgSO4
  7. concentrationconcentrated to dryness
  8. custompurified via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-52208ae558b6467c8f378a6949427b4f
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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