Ethyl Acetate → HCID 178435478, compound

HRID 2371686Notes

Reaction equation

HRID 2371686 reaction equation
[C:1]([N:3]=C(OCC)C)#[N:2].[C:9]([C:11]1[CH:31]=[CH:30][C:14]2[O:15][C:16]([CH3:29])([CH3:28])[C@@H:17]([OH:27])[C@H:18]([NH:19][CH2:20][C:21]3C=CC=CC=3)[C:13]=2[CH:12]=1)#N.[C:32](OCC)(=O)C>>[C:9]([C:11]1[CH:31]=[CH:30][C:14]2[O:15][C:16]([CH3:28])([CH3:29])[C@@H:17]([OH:27])[C@H:18]([NH:19][C:20](=[N:3][C:1]#[N:2])[CH3:21])[C:13]=2[CH:12]=1)#[CH:32]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 258806Ethyl N-cyanoethanimideateHCID 67841350HCID 67841350, compound

Product 1

HCID 178435478HCID 178435478, compound

Procedure

To 1.54 g of ethyl N-cyanoacetimidate, 3.86 g of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-benzylamino-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 purified by silica gel chromatography to obtain 1.65 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 purified by silica gel chromatography
  7. customto obtain 1.65 g of the

Sources & evidence

ORD record
ord-98de09812e3043bc84d9ef72fdf6a309
Source dataset
uspto-grants-1992_03
Patent number
US05095016

Reaction notes

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