Ethyl N-cyanoethanimideate → HCID 178464619, compound

HRID 1030216Notes

Reaction equation

HRID 1030216 reaction equation
[NH2:1][C@@H:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:15])([CH3:14])[C@H:3]1[OH:16].[C:17]([N:19]=[C:20](OCC)[CH3:21])#[N:18]>N1C=CC=CC=1>[C:17]([N:19]=[C:20]([NH:1][C@@H:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:14])([CH3:15])[C@H:3]1[OH:16])[CH3:21])#[N:18]

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, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of trans-4-amino-3,4-dihydro-2,2-dimethyl-3-hydroxy-2H-1-benzopyran-6-carbonitrile (15.28 g) and ethyl N-cyanoacetimidate (9.42 g) in pyridine (70 ml) was refluxed under nitrogen atmosphere for 9 hours. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (150 ml), washed with 5% hydrochloric acid (100 ml), water (100 ml), and brine (100 ml), successively. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give trans-4-[N-[1-(cyanoimino)ethyl]amino]-3,4-dihydro-2,2-dimethyl-3-hydroxy-2H-1-benzopyran-6-carbonitrile (12.68 g).

Workup

  1. temperaturewas refluxed under nitrogen atmosphere for 9 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (150 ml)
  4. washwashed with 5% hydrochloric acid (100 ml), water (100 ml), and brine (100 ml)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0f57c9898f9145e1b239b195ed579b9d
Source dataset
uspto-grants-1992_04
Patent number
US05104890

Reaction notes

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