Hydrochloric Acid → HCID 21256660, compound

HRID 635829Notes

Reaction equation

HRID 635829 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:15][CH:14]=[CH:13][CH2:12][C@H:11]2[N+]([O-])=O)=[CH:6][C:5]=1[O:19][CH2:20][CH3:21])[CH3:2].[O-:22]CC.[Na+].Cl.NC(N)=O>C(O)C.O>[CH2:20]([O:19][C:5]1[CH:6]=[C:7]([CH:10]2[CH2:15][CH:14]=[CH:13][CH2:12][C:11]2=[O:22])[CH:8]=[CH:9][C:4]=1[O:3][CH2:1][CH3:2])[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 2723922Sodium ethoxideHCID 54371924HCID 54371924, compound

Product 1

HCID 21256660HCID 21256660, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

15.0 g of (+/−)-trans-1,2-diethoxy-4-(2-nitrocyclohex-4-enyl)benzene are dissolved in 375 ml of ethanol and added dropwise to 42 ml of 20% strength sodium ethoxide solution. The mixture is stirred at RT for 20 min. and then added dropwise to an ice-cooled solution of 67.5 ml of conc. hydrochloric acid and 1.35 g of urea in 225 ml of water and 170 ml of ethanol. The solution is extracted with water/dichloromethane and the organic phase is dried with sodium sulfate and concentrated under reduced pressure. The residue is chromatographed over silica gel using petroleum ether/ethyl acetate in a ratio of 2/1. Concentration of the appropriate eluate fractions gives 10.33 g (77.1% of Th.) of the title compound as an oil.

Workup

  1. extractionThe solution is extracted with water/dichloromethane
  2. dry with materialthe organic phase is dried with sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-53ccccdaaad640519f0681a0141c15f7
Source dataset
uspto-grants-2001_02
Patent number
US06191138B1

Reaction notes

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