Ethyl N-cyanoethanimideate → HCID 15042117, compound

HRID 2371685Notes

Reaction equation

HRID 2371685 reaction equation
[C:1]([N:3]=[C:4](OCC)[CH3:5])#[N:2].[C:9]([C:11]1[CH:25]=[CH:24][C:14]2[O:15][C:16]([CH3:23])([CH3:22])[C@@H:17]([OH:21])[C@H:18]([NH:19][CH3:20])[C:13]=2[CH:12]=1)#[N:10]>C(OCC)(=O)C>[C:9]([C:11]1[CH:25]=[CH:24][C:14]2[O:15][C:16]([CH3:22])([CH3:23])[C@@H:17]([OH:21])[C@H:18]([N:19]([C:4](=[N:3][C:1]#[N:2])[CH3:5])[CH3:20])[C:13]=2[CH:12]=1)#[N:10]

Participants

4

Reactant 2

HCID 258806Ethyl N-cyanoethanimideateHCID 15634838HCID 15634838, compound

Product 1

HCID 15042117HCID 15042117, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 2.80 g of ethyl N-cyanoacetimidate, 4.65 g of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-methylamino-2H-benzo[b]pyran-3-ol was added, and the mixture was reacted under stirring at a temperature of from 100° to 120° C. for 2 hours. The reaction mixture was cooled, then dissolved in 100 ml of ethyl acetate, washed twice with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The residual solid was recrystallized from ethanol to obtain 2.34 g of the above identified compound in the form of crystals.

Workup

  1. customthe mixture was reacted
  2. temperatureThe reaction mixture was cooled
  3. washwashed twice with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, ethyl acetate was distilled off under reduced pressure
  6. customThe residual solid was recrystallized from ethanol
  7. customto obtain 2.34 g of the

Sources & evidence

ORD record
ord-e5b148f2f3184ea38284c10d2fcee6c5
Source dataset
uspto-grants-1992_03
Patent number
US05095016

Reaction notes

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