Methanimidic acid, N-cyano-, ethyl ester → HCID 178431173, compound

HRID 2371679Notes

Reaction equation

HRID 2371679 reaction equation
[C:1]([N:3]=[CH:4]OCC)#[N:2].[C:8]([C:10]1[CH:23]=[CH:22][C:13]2[O:14][C:15]([CH3:21])([CH3:20])[C@@H:16]([OH:19])[C@H:17]([NH2:18])[C:12]=2[CH:11]=1)#[N:9]>C(OCC)(=O)C>[C:8]([C:10]1[CH:23]=[CH:22][C:13]2[O:14][C:15]([CH3:21])([CH3:20])[C@@H:16]([OH:19])[C@H:17]([NH:18][CH:4]=[N:3][C:1]#[N:2])[C:12]=2[CH:11]=1)#[N:9]

Participants

4

Reactant 2

HCID 9920370Methanimidic acid, N-cyano-, ethyl esterHCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

Product 1

HCID 178431173HCID 178431173, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 1.18 g of ethyl N-cyanoformimidate, 2.29 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 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 methylene chloride/isopropanol/petroleum ether to obtain 1.75 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 methylene chloride/isopropanol/petroleum ether
  7. customto obtain 1.75 g of the

Sources & evidence

ORD record
ord-b5aa01a447564fe9babdf637aa38aa53
Source dataset
uspto-grants-1992_03
Patent number
US05095016

Reaction notes

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