Carbon Disulfide → HCID 18668831, compound

HRID 1058568Notes

Reaction equation

HRID 1058568 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[H-].[Na+].[C:8](=[S:10])=[S:9].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1>C1C=CC=CC=1.CN(C=O)C>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][S:9][C:8](=[C:2]([C:1]#[N:5])[C:3]#[N:4])[S:10][CH2:17][C:16]2[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 8010MalononitrileHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 18668831HCID 18668831, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

DMF (40 mL) was slowly added to a rapidly stirred mixture of malononitrile (13.2 g, 0.2 mol) and NaH (9.6 g, 0.4 mol) and CS2 (22.8 g, 0.3 mol) in benzene (200 mL). The reaction mixture was stirred at room temperature for 30 min and 4-methoxybenzyl chloride (93.6 g, 0.6 mol) was added. The resulting mixture was stirred for 12 h, and benzene (50 mL) and ice-water (200 mL) were added. The organic layer was separated, dried, and concentrated in vacuum. The product was purified by flash chromatography on silica gel, eluting with ethyl acetate:hexanes (15:85). Yield: 45.8 g (0.12 mol, 60%). NMR (δ, CDCl3): 7.22 (4H, d, J=8.6 Hz); 6.85 (4H, d, J=8.6 Hz); 4.33 (4H, s); 3.79 (6H, s).

Workup

  1. stirringThe resulting mixture was stirred for 12 h
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated in vacuum
  5. customThe product was purified by flash chromatography on silica gel
  6. washeluting with ethyl acetate:hexanes (15:85)

Sources & evidence

ORD record
ord-e5d1ad4ad9ff407288a13db9ba73f650
Source dataset
uspto-grants-2003_02
Patent number
US06518266B1

Reaction notes

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