Sodium Iodide → HCID 57855907, compound

HRID 2039598Notes

Reaction equation

Br[CH:2](Br)[C:3]1[C:8]([CH:9](Br)Br)=[N:7][CH:6]=[CH:5][N:4]=1.[C:13]([O:22][CH2:23][CH3:24])(=[O:21])/[CH:14]=[CH:15]\[C:16]([O:18][CH2:19][CH3:20])=[O:17].[Na+].[I-]>CN(C=O)C>[CH2:23]([O:22][C:13]([C:14]1[CH:2]=[C:3]2[C:8](=[CH:9][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:7]=[CH:6][CH:5]=[N:4]2)=[O:21])[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 38.0 g (90.0 mmol) 2,3-bis-dibromomethyl-pyrazine and 70.0 g (400 mmol) diethyl maleate in 450 ml DMF is added 40.0 g (270.0 mmol) NaI and the mixture is heated at a temperature of 80° C. during 20 hours. After evaporation of the solvent, the residue is dissolved in 1000 ml t-butyl-methyl ether and washed with a 5% sodium thiosulfate solution and water (5 times). Evaporation of the solvent and purification of the residue with flash-chromatography yielded 9.1 g dark oil (37%). 1H-NMR (CDCl3, 400 MHz): 1.45 ppm (t, 6H), 4.45 (q, 4H), 8.5 (s, 2H), 9.0 (s, 2H).

Workup

customAfter evaporation of the solvent
dissolutionthe residue is dissolved in 1000 ml t-butyl-methyl ether
washwashed with a 5% sodium thiosulfate solution and water (5 times)
customEvaporation of the solvent and purification of the residue with flash-chromatography

Sources & evidence

ORD record: ord-d94b3f08e1c2463e97f2fb4de46a4a7f
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580785B2

Reaction notes

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