Hydrochloric Acid → HCID 69745618, compound

HRID 1816191Notes

Reaction equation

HRID 1816191 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.II.Cl>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5](/[C:6](/[C:7]#[N:8])=[C:6](\[C:5]2[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=2)/[C:7]#[N:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 807IodineHCID 27914Benzeneacetonitrile, 4-bromo-

Product 1

HCID 69745618HCID 69745618, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

More specifically, 4-bromobenzyl cyanide was oxidized with iodine and hydrolyzed with 3% HCl (aq)/THF to form bis(4-bromophenyl)maleonitrile (40˜50%). See Cook & Linstead (1937) J. Chem. Soc. 929. Bis(4-bromophenyl)maleonitrile thus obtained was alkylated with KotBu/CH3I to afford N-methyl-bis(4-bromophenyl)maleimide (86%). NPAMLI was prepared by palladium catalyzed amination of N-methyl-bis(4-bromophenyl)maleimide (71%), followed by column chromatography and sublimation purification. The synthetic data of the synthesized compounds are listed below:

Sources & evidence

ORD record
ord-8138e32843c543f7a2102c1b8798196d
Source dataset
uspto-grants-2005_04
Patent number
US06884525B2

Reaction notes

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