HCID 19858390, compound → HCID 20195686, compound

HRID 653172Notes

Reaction equation

HRID 653172 reaction equation
[C:1]1([O-:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(C)=O.[CH:12]1[C:15]2[CH:16]=[CH:17][C:18]([N:20]3[C:24](=[O:25])[C:23]4=[CH:26][C:27]([N+]([O-])=O)=[CH:28][CH:29]=[C:22]4[C:21]3=[O:33])=[CH:19][C:14]=2[CH:13]=1>O>[CH:12]1[C:15]2[CH:16]=[CH:17][C:18]([N:20]3[C:24](=[O:25])[C:23]4=[CH:26][C:27]([O:7][C:1]5[CH:6]=[CH:5][CH:4]=[C:3]([C:12]#[C:13][C:14]6[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=6)[CH:2]=5)=[CH:28][CH:29]=[C:22]4[C:21]3=[O:33])=[CH:19][C:14]=2[CH:13]=1

Participants

4

Reactant 2

HCID 19858390HCID 19858390, compoundHCID 86741634HCID 86741634, compound

Product 1

HCID 20195686HCID 20195686, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

The dark phenolate/DMSO solution was allowed to cool to about 35° C. in an oil bath. N-4-benzocyclobutenyl 4-nitrophthalimide (1.00g, 3.40 mmol) was added next. The resultant reaction mixture was stirred under N2 at 30°-35° C. for another 21/2 hours. Then, the reaction mixture was poured into a separatory funnel containing about 300 ml of H2O and extracted with ethyl acetate (100 ml, 3×50 ml). The organic extract was then washed with saturated NaCl solution (2×150 ml) and dried over MgSO4. The volume of the dried extract was concentrated on a rotary evaporator to about 10 ml and passed through a chromatographic column containing about 100 g of silica gel saturated with petroleum ether. Elution was carried out with 100 ml petroleum ether, followed by 1:2 CH2Cl2 / petroleum ether. 4 bands were developed in the column. The desired product which was contained in the first band, was isolated as light yellow microcrystals. Yield: 0.45 g (30%). Calc. for C30H19NO3 : 81.62% C; 4.34% H; 3.17% N. Found: 81.05% C; 4.31% H; 3.09% N. Mass Spectroscopy: 441 (M+, 100%). Proton NMR (CDCl3): 3.20 (singlet, alicyclic protons); 7.00-7.93, (complex, aromatic protons). IR(KBr): 2700 m (alicyclic C--H stretches); 1706 m, 1778 vs (symmetric and asymmetric stretches of imide group): 1238 ms (Ar--O--Ar stretch).

Workup

  1. customThe resultant reaction mixture
  2. additionThen, the reaction mixture was poured into a separatory funnel
  3. extractionextracted with ethyl acetate (100 ml, 3×50 ml)
  4. extractionThe organic extract
  5. washwas then washed with saturated NaCl solution (2×150 ml)
  6. dry with materialdried over MgSO4
  7. extractionThe volume of the dried extract
  8. concentrationwas concentrated on a rotary evaporator to about 10 ml
  9. additioncontaining about 100 g of silica gel saturated with petroleum ether
  10. washElution
  11. customwas isolated as light yellow microcrystals
  12. custom1238 ms (Ar--O--Ar stretch)

Sources & evidence

ORD record
ord-27c87fc3fcd548f3b61cdbc228256365
Source dataset
uspto-grants-1987_06
Patent number
US04675370

Reaction notes

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