ethyl N-cyanopropionimidate → HCID 178457586, compound

HRID 1030218Notes

Reaction equation

HRID 1030218 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)[CH2:21][CH3:22])#[N:18]>C(O)C>[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])[CH2:21][CH3:22])#[N:18]

Participants

4

Reactant 2

HCID 10820532ethyl N-cyanopropionimidateHCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

Product 1

HCID 178457586HCID 178457586, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of trans-4-amino-3,4-dihydro-2,2-dimethyl-3-hydroxy-2H-1-benzopyran-6-carbonitrile (4.37 g) and ethyl N-cyanopropionimidate (2.65 g) in ethanol (22 ml) was refluxed for 10 hours. The mixture was cooled and concentrated under reduced pressure. The residue was pulverized with ethanol and recrystallized from ethanol to give trans-4-[N-[1-(cyanoimino)propyl]amino]-3,4-dihydro-2,2-dimethyl-3-hydroxy-2H-1-benzopyran-6-carbonitrile (2.81 g).

Workup

  1. temperaturewas refluxed for 10 hours
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ef8b4c26a3324654b19cb9e0070fa59c
Source dataset
uspto-grants-1992_04
Patent number
US05104890

Reaction notes

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