Ethyl N-cyanoethanimideate → HCID 178464619, compound

HRID 2371680Notes

Reaction equation

HRID 2371680 reaction equation
[C:1]([N:3]=[C:4](OCC)[CH3:5])#[N:2].[C:9]([C:11]1[CH:24]=[CH:23][C:14]2[O:15][C:16]([CH3:22])([CH3:21])[C@@H:17]([OH:20])[C@H:18]([NH2:19])[C:13]=2[CH:12]=1)#[N:10]>C(OCC)(=O)C>[C:9]([C:11]1[CH:24]=[CH:23][C:14]2[O:15][C:16]([CH3:22])([CH3:21])[C@@H:17]([OH:20])[C@H:18]([NH:19][C:4](=[N:3][C:1]#[N:2])[CH3:5])[C:13]=2[CH:12]=1)#[N:10]

Participants

4

Reactant 2

HCID 258806Ethyl N-cyanoethanimideateHCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

Product 1

HCID 178464619HCID 178464619, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 1.23 g of ethyl N-cyanoacetimidate, 2.18 g of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-amino-2H-benzo[b]pyran-3-ol was added, and the mixture was stirred 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 oily substance was recrystallized from ethyl acetate/n-hexane to obtain 1.75 g of the above identified compound in the form of crystals.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed twice with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThen, ethyl acetate was distilled off under reduced pressure
  5. customThe residual oily substance was recrystallized from ethyl acetate/n-hexane
  6. customto obtain 1.75 g of the

Sources & evidence

ORD record
ord-e267c8f49b934a6392ad57625c30e4fa
Source dataset
uspto-grants-1992_03
Patent number
US05095016

Reaction notes

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