Water → HCID 15523941, compound

HRID 1978014Notes

Reaction equation

HRID 1978014 reaction equation
[NH2:1][CH2:2][CH:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6][C:5]1([CH3:17])[CH3:16].[C:18]([N:22]=[C:23]=[O:24])([CH3:21])([CH3:20])[CH3:19].O.C(OCC)(=O)C>C1COCC1>[C:18]([NH:22][C:23](=[O:24])[NH:1][CH2:2]/[CH:3]=[C:4]1/[C:5]([CH3:17])([CH3:16])[CH2:6][CH2:7][C:8]2[C:13]/1=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 62412tert-Butyl isocyanateHCID 54433053HCID 54433053, compound

Product 1

HCID 15523941HCID 15523941, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-aminoethylidene)-7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene (1.5 g, 6.48 mmol) in THF (30 ml) was gradually added dropwise, under ice-cooling, Tert-butyl isocyanate (0.84 g, 8.43 mmol). The mixture was stirred for 2 hours at room temperature. The reaction mixture was then poured into water. The organic layer was subjected to ethyl acetate. The extract solution was washed with brine and water, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=8:2),-followed by recrystallization to give the above-titled compound (yield 780 mg, 36%), m.p.175-176° C. (recrystallized from ethyl acetate/diethyl ether).

Workup

  1. temperaturecooling
  2. washThe extract solution was washed with brine and water, which
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationby distilling off the solvent under reduced pressure
  5. customThe residue was purified by means of a silica gel column chromatography (hexane
  6. customethyl acetate=8:2),-followed by recrystallization
  7. customto give
  8. customthe above-titled compound (yield 780 mg, 36%), m.p.175-176° C. (recrystallized from ethyl acetate/diethyl ether)

Sources & evidence

ORD record
ord-18cb6f85b2444cf88c680d27cff23365
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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