4-Nitrobenzyl bromide → HCID 86234940, compound

HRID 2414118Notes

Reaction equation

HRID 2414118 reaction equation
[Na][Na].[C:3]([NH:5][C:6](=[O:15])[CH2:7][CH2:8][CH2:9][C:10]([NH:12][C:13]#[N:14])=[O:11])#[N:4].[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1)([O-:18])=[O:17]>CN(C)C=O>[C:13]([N:12]([CH2:23][C:22]1[CH:25]=[CH:26][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=1)[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:6]([N:5]([CH2:23][C:22]1[CH:25]=[CH:26][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=1)[C:3]#[N:4])=[O:15])#[N:14]

Participants

5

Reactant 3

HCID 660114-Nitrobenzyl bromideHCID 141233DisodiumHCID 88642675HCID 88642675, compound

Product 1

HCID 86234940HCID 86234940, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

22.4 g (0.1 mol) of the disodium salt of glutaric acid bis-(N-cyanamide) and 51.85 g (0.2 mol+20% excess) of 4-nitrobenzyl bromide are reacted in 120 ml of dimethylformamide at 36°-40° C. for 1 hour and the mixture is worked up in a manner similar to that in Example 2. 44.3 g (98.4% of theory) of a yellowish crystalline crude product are obtained, and are recrystallised from 440 ml of ethyl acetate. 31.5 g (70.0% of theory) of a colourless, crystalline product of a melting point 146.2°-148.2° C. are obtained.

Sources & evidence

ORD record
ord-fb3a4decb5a94527967130f8cdef1bb9
Source dataset
uspto-grants-1988_01
Patent number
US04721770

Reaction notes

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