Sodium Nitrite → HCID 25017231, compound

HRID 1785607Notes

Reaction equation

HRID 1785607 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][N:12]2[CH:16]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH2:15][NH:14][C:13]2=[O:25])=[CH:5][CH:4]=1.[N:26]([O-])=O.[Na+]>C(O)(=O)C.O.[Zn]>[NH2:26][N:14]1[CH2:15][CH:16]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[N:12]([CH2:11][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:13]1=[O:25]

Participants

6

Reactant 2

HCID 23668193Sodium NitriteHCID 44541741HCID 44541741, compound

Product 1

HCID 25017231HCID 25017231, compoundYield 109.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 1-[3-(4-methoxyphenyl)propyl]-5-[(4-methoxy)-phenyl]-2-imidazolidinone (0.6 g, 1.75 mmol) in acetic acid (15 mL) is added dropwise a solution of NaNO2 (0.12 g, 1.8 mmol) in water (1 mL). The mixture is cooled in an ice bath to 5° C. and zinc dust (0.6 g, 9 mmol) is added in portions (starting with 0.5 g addition) over 50 minutes at less than 12° C. The reaction is stirred for 5 minutes and the ice bath is removed. The reaction temperature rises quickly to about 20° C. and the reaction is maintained below about 32° C. with an ice bath. The reaction is stirred for 70 minutes at 20° C. to 27° C. and any unreacted zinc is removed by filtration. The volume of the filtrate is reduced in vacuo then diluted with dichloromethane (15 mL). To the stirred mixture is added concentrated ammonium hydroxide (2 mL), keeping the temperature below about 32° C. with an ice bath. The organic phase is separated, washed with brine, dried (Na2SO4), and concentrated to afford 0.68 g (quantitative yield) of the desired compound as a colorless oil which is used without further purification.

Workup

  1. customthe ice bath is removed
  2. customrises quickly to about 20° C.
  3. temperaturethe reaction is maintained below about 32° C. with an ice bath
  4. stirringThe reaction is stirred for 70 minutes at 20° C. to 27° C.
  5. customany unreacted zinc is removed by filtration
  6. additionthen diluted with dichloromethane (15 mL)
  7. additionTo the stirred mixture is added concentrated ammonium hydroxide (2 mL)
  8. customthe temperature below about 32° C.
  9. customThe organic phase is separated
  10. washwashed with brine
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-e35e3c5e220b4586b435a236b43a5731
Source dataset
uspto-grants-2009_03
Patent number
US07504517B2

Reaction notes

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