HCID 70584365, compound → HCID 70605998, compound

HRID 1390806Notes

Reaction equation

HRID 1390806 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:9](=[O:10])[C@H:8]([NH:11][C:12](=[O:21])[CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@@H:7]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH:28]1[O:32][CH2:31][CH2:30][O:29]1>C(#N)C.O>[O:29]1[CH2:30][CH2:31][O:32][CH:28]1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C@H:7]1[C@@H:8]([NH:11][C:12](=[O:21])[CH2:13][O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:9](=[O:10])[NH:6]1

Participants

4

Reactant 1

HCID 70584365HCID 70584365, compound

Product 1

HCID 70605998HCID 70605998, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The product of Example 4 (1.56 g, 3 mmol) was dissolved in a mixture of acetonitrile (120 ml) and distilled water (30 ml), degassed with argon for 30 minutes, and brought to reflux. A degassed solution of K2S2O8 (5.67 g, 21 mmol) and Na2HPO4.7H2O (2.81 g, 10.5 mmol) in distilled water (120 ml) was added in 8 equal portions at 4 minute intervals to the refluxing solution, the reaction being kept at pH >6 by the addition of solid Na2HPO4.7H2O. The acetonitrile was evaporated and the residue was extracted with ethyl acetate. The extracts were washed with brine, dried, and evaporated to an oil, 2.07 g. The oil was extracted with petroleum ether to remove the dimethoxybenzaldehyde and then was triturated with ethyl acetate-ether. It was cooled in ice and the resulting solid product was collected; 0.54 g (49%), mp 137-138° dec.

Workup

  1. distillationdistilled water (30 ml)
  2. customdegassed with argon for 30 minutes
  3. temperatureto reflux
  4. customThe acetonitrile was evaporated
  5. extractionthe residue was extracted with ethyl acetate
  6. washThe extracts were washed with brine
  7. customdried
  8. customevaporated to an oil, 2.07 g
  9. extractionThe oil was extracted with petroleum ether
  10. customto remove the dimethoxybenzaldehyde
  11. customwas triturated with ethyl acetate-ether
  12. temperatureIt was cooled in ice
  13. customthe resulting solid product was collected

Sources & evidence

ORD record
ord-16af24270a614c1895a8e3296db59dc3
Source dataset
uspto-grants-1979_02
Patent number
US04140688

Reaction notes

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