Sodium hydride → 2818-06-6

HRID 1978920Notes

Reaction equation

HRID 1978920 reaction equation
CC1C=CC(S([CH2:11][N+:12]#[C-:13])(=O)=O)=CC=1.[C:14]([O:22][CH3:23])(=[O:21])/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18].[H-].[Na+]>CN(C=O)C>[NH:12]1[CH:13]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[C:15]([C:14]([O:22][CH3:23])=[O:21])=[CH:11]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanideHCID 637568Dimethyl Fumarate

Product 1

HCID 50873262818-06-6

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

TOSMIC (1.5 g, 7.7 mmol) was added to a solution of dimethyl fumarate (1 g, 6.9 mmol) and sodium hydride (60%, 0.59, 12.5 mmol) in dry DMF (25 ml) at 0° C., and the solution stirred at 0° C. for 15 minutes. The reaction was poured onto ice-water and the product filtered and recrystallised from aqueous ethanol. 0.61 g, 48%. 1H-n.m.r. (DMSO-d6) δ (ppm) 3.68 (6H, s, 2×CH3), 7.39 (2H, s, 2×CH), 11.81 (1H, s, NH).

Workup

  1. additionThe reaction was poured onto ice-water
  2. filtrationthe product filtered
  3. customrecrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-a009546adac7428ebb42b87d9cf41f2e
Source dataset
uspto-grants-2001_05
Patent number
US06239159B1

Reaction notes

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