Sodium Hydroxide → HCID 22471773, compound

HRID 1004650Notes

Reaction equation

HRID 1004650 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=3)[C:11]2=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.[Sn](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>C(O)C>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([N:12]2[CH:13]=[CH:14][N:10]([CH2:9][CH2:8][CH2:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:11]2=[O:24])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 22471753HCID 22471753, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 22471773HCID 22471773, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

1-(3-Cyclohexyl-propyl)-3-(4-nitro-phenyl)-1,3-dihydro-imidazol-2-one (15.4 g, 46.8 mmol) and tin chloride dihydrate (53.0 g, 234.5 mmol, 5.0 equiv) were combined in ethanol and heated at 70° C. for two hours. The mixture was cooled to 25° C. and poured onto ice (500 mL). The aqueous mixture was adjusted to pH=8 with 1 N aqueous sodium hydroxide solution. The aqueous phase was extracted with ethyl acetate (3×). The combined organic phase was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated in vacuo to an orange solid (13.4 g, 95%). Mp 83-85° C.; 1H NMR (CDCl3, 300 MHz) δ 7.26 (d, 8.5 Hz, 2 H), 6.64 (d, 8.5 Hz, 2 H), 6.40 (d, 2.9 Hz, 1 H), 6.24 (d, 2.9 Hz, 1 H), 3.70 (br s, 2 H), 3.57 (t, 7.4 Hz, 2 H), 1.64 (m, 7 H), 1.19 (m, 6 H), 0.85 (m, 2 H); MS (CI) m/z 300 (MH+); Rf =0.24 (50:50 hexane/ethyl acetate).

Workup

  1. temperatureThe mixture was cooled to 25° C.
  2. additionpoured onto ice (500 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×)
  4. washThe combined organic phase was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo to an orange solid (13.4 g, 95%)

Sources & evidence

ORD record
ord-7ee73217737648e18af5ca2823eb3384
Source dataset
uspto-grants-2000_04
Patent number
US06051586

Reaction notes

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