Allyl bromide → N,N-diallyl-4,4'-dinitro-2-biphenylamine

HRID 891837Notes

Reaction equation

HRID 891837 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:19])[C:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH2:20](Br)[CH:21]=[CH2:22].C(=O)([O-])[O-].[K+].[K+].CN1C(=O)[CH2:34][CH2:33][CH2:32]1>>[CH2:20]([N:19]([CH2:34][CH:33]=[CH2:32])[C:6]1[C:7]([C:10]2[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=2)=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH:21]=[CH2:22]

Participants

5

Reactant 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 932654,4'-Dinitro(1,1'-biphenyl)-2-amine

Product 1

HCID 22239440N,N-diallyl-4,4'-dinitro-2-biphenylamine

Procedure

A mixture of 4,4′-dinitro-2-biphenylamine (10.0 g), allyl bromide (20 mL), potassium carbonate (16 g) and NMP (100 mL) was heated to 90–95° C. for 90 hr. The mixture was extracted with tetrahydrofuran (THF)-ethyl acetate-water and purified by crystallization from ethyl acetate to give N,N-diallyl-4,4′-dinitro-2-biphenylamine (7.0 g).

Workup

  1. temperaturewas heated to 90–95° C. for 90 hr
  2. extractionThe mixture was extracted with tetrahydrofuran (THF)-ethyl acetate-water
  3. custompurified by crystallization from ethyl acetate

Sources & evidence

ORD record
ord-b81fa3ea0896455a9213f204d9adc483
Source dataset
uspto-grants-2006_02
Patent number
US07005165B2

Reaction notes

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