Sodium Carbonate → HCID 90426751, compound

HRID 2278950Notes

Reaction equation

HRID 2278950 reaction equation
Cl.[F:2][C:3]1([F:10])[CH2:8][CH2:7][CH:6]([NH2:9])[CH2:5][CH2:4]1.C([O-])([O-])=O.[Na+].[Na+].Cl[CH2:18][CH2:19][N:20]=[C:21]=[O:22].[H-].[Na+]>C1COCC1>[F:2][C:3]1([F:10])[CH2:8][CH2:7][CH:6]([N:9]2[CH2:18][CH2:19][NH:20][C:21]2=[O:22])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 160352-Chloroethyl isocyanateHCID 24758Sodium hydrideHCID 231506694,4-Difluorocyclohexan-1-amine hydrochloride

Product 1

HCID 90426751HCID 90426751, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4,4-difluorocyclohexanamine hydrochloride (0.800 g, 4.66 mmol) in THF (20 mL) was treated with Na2CO3 (0.800 g, 7.55 mmol) followed by 1-chloro-2-isocyanatoethane (0.800 g, 7.58 mmol) and stirred at RT for 2 h. The mixture was cooled to 0° C., treated with NaH (60% in mineral oil, 0.300 g, 7.50 mmol), warmed to RT and stirred for 4 h. The mixture was poured into satd. NH4Cl solution, the layers separated and the aqueous layer extracted with DCM (3×). The combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford 1-(4,4-difluorocyclohexyl)imidazolidin-2-one (624 mg, 66%) as a white solid. MS (ESI) m/z: 205.1 (M+H+).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. temperaturewarmed to RT
  3. stirringstirred for 4 h
  4. additionThe mixture was poured into satd
  5. customNH4Cl solution, the layers separated
  6. extractionthe aqueous layer extracted with DCM (3×)
  7. washThe combined organics were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2ad40bbf21004942aa4b3f5245374114
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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