Sodium hydride → HCID 178431170, compound

HRID 704781Notes

Reaction equation

HRID 704781 reaction equation
[C:1]([N:3]=[C:4]1[NH:8][CH2:7][CH2:6][NH:5]1)#[N:2].[H-].[Na+].[O:11]1[CH:17]2[CH:12]1[C:13]([CH3:25])([CH3:24])[O:14][C:15]1[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][C:16]=12>CS(C)=O>[C:1]([N:3]=[C:4]1[NH:8][CH2:7][CH2:6][N:5]1[C@@H:17]1[C:16]2[CH:18]=[C:19]([C:22]#[N:23])[CH:20]=[CH:21][C:15]=2[O:14][C:13]([CH3:24])([CH3:25])[C@H:12]1[OH:11])#[N:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochromanHCID 178512073HCID 178512073, compound

Product 1

HCID 178431170HCID 178431170, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of 2-cyanoiminoimidazolidine (0.42 g) in dimethyl sulfoxide (12.5 ml) was added 60% sodium hydride (0.15 g) under water-cooling and the mixture was stirred at room temperature for 0.5 hours. 3,4-Epoxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.50 g) was added portionwise thereto. After being stirred at room temperature overnight, the mixture was poured into ice-brine (50 ml) and extracted with ethyl acetate (50 ml). The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was pulverized with chloroform and recrystallized from ethanol to give trans-4-(2-cyanoiminoimidazolidin-1-yl)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.15

Workup

  1. temperaturecooling
  2. stirringAfter being stirred at room temperature overnight
  3. extractionextracted with ethyl acetate (50 ml)
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-48c666116ff147e0922ee5eb69bb821b
Source dataset
uspto-grants-1991_01
Patent number
US04988723

Reaction notes

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