Sodium hydride → HCID 20073264, compound

HRID 704791Notes

Reaction equation

HRID 704791 reaction equation
[H-].[Na+].[C:3]([N:5]=[C:6]1[NH:10][CH2:9][CH2:8][N:7]1[CH2:11][CH3:12])#[N:4].O1[CH:19]2[CH:14]1[C:15]([CH3:27])([CH3:26])[O:16][C:17]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][C:18]=12>CS(C)=O>[C:3]([N:5]=[C:6]1[N:7]([CH2:11][CH3:12])[CH2:8][CH2:9][N:10]1[C:19]1[C:18]2[CH:20]=[C:21]([C:24]#[N:25])[CH:22]=[CH:23][C:17]=2[O:16][C:15]([CH3:27])([CH3:26])[CH:14]=1)#[N:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochromanHCID 178462644HCID 178462644, compound

Product 1

HCID 20073264HCID 20073264, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
40 °C

Procedure

60% Dispersion of sodium hydride (0.40 g) in mineral oil was added in small portion at ambient temperature to a solution of 2-cyanoimino-1-ethylimidazolidine (1.38 g) in dimethyl sulfoxide (15 ml). The reaction mixture was stirred for 30 minutes at the same temperature, and 3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (1.01 g) was added thereto. The reaction mixture was stirred overnight at the same temperature, heated for 1.5 hours at 40° C., and then poured into ice-water (50 ml). The forming precipitate was collected by filtration, and washed with water. The product was recrystallized from ethanol to give 4-(2-cyanoimino-3-ethylimidazolidin-1-yl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.36 g).

Workup

  1. additionwas added
  2. filtrationThe forming precipitate was collected by filtration
  3. washwashed with water
  4. customThe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-155a2601655543f48e6593784c02d74d
Source dataset
uspto-grants-1991_01
Patent number
US04988723

Reaction notes

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