Benzene → HCID 178464609, compound

HRID 2371688Notes

Reaction equation

HRID 2371688 reaction equation
[C:1]([C:3]1[CH:25]=[CH:24][C:6]2[O:7][C:8]([CH3:23])([CH3:22])[C@@H:9](OS(C)(=O)=O)[C@H:10]([NH:11][C:12](=[N:14][C:15]#[N:16])[CH3:13])[C:5]=2[CH:4]=1)#[N:2].C1C=CC=CC=1>C(OCC)(=O)C>[C:1]([C:3]1[CH:25]=[CH:24][C:6]2[O:7][C:8]([CH3:22])([CH3:23])[CH:9]=[C:10]([NH:11][C:12](=[N:14][C:15]#[N:16])[CH3:13])[C:5]=2[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 241BenzeneHCID 178464620HCID 178464620, compound

Product 1

HCID 178464609HCID 178464609, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 15 g of 6-cyano-3,4-dihydro-3-methanesulfonyloxy-2,2-dimethyl-trans-4-[(N-cyano-acetimidoyl)amino]-2H-benzo[b]pyran obtained in Step (1) of Example 34, 300 ml of benzene and then 18 g of 1,8-diazabicyclo(5,4,0]-7-undecene were added, and the mixture was reacted under reflux for 3 hours. The reaction mixture was cooled to room temperature, then diluted by addition of 200 ml of ethyl acetate and then washed three times with water. The benzene/ethyl acetate extract solution was dried over anhydrous sodium sulfate. Then, benzene and ethyl acetate were distilled off under reduced pressure. The residual solid was recrystallized from ethanol to obtain 9.3 g of the above identified compound in the form of crystals.

Workup

  1. customthe mixture was reacted
  2. temperatureunder reflux for 3 hours
  3. washwashed three times with water
  4. extractionThe benzene/ethyl acetate extract solution
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. distillationThen, benzene and ethyl acetate were distilled off under reduced pressure
  7. customThe residual solid was recrystallized from ethanol
  8. customto obtain 9.3 g of the

Sources & evidence

ORD record
ord-dfc28947ab174939a499ab4bd2d8d5f8
Source dataset
uspto-grants-1992_03
Patent number
US05095016

Reaction notes

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