Isopropylamine → N-Isopropyl-3,4-dimethyl-2,6-dinitroaniline

HRID 903477Notes

Reaction equation

HRID 903477 reaction equation
Cl[C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]([CH3:12])[C:5]([CH3:11])=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH:16]([NH2:19])([CH3:18])[CH3:17]>>[CH:16]([NH:19][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH3:11])=[C:4]([CH3:12])[C:3]=1[N+:13]([O-:15])=[O:14])([CH3:18])[CH3:17]

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 134551024-Chloro-3,5-dinitro-o-xylene

Product 1

HCID 12767671N-Isopropyl-3,4-dimethyl-2,6-dinitroanilineYield 80%

Procedure

4-Chloro-3,5-dinitro-o-xylene (10.0 grams, 0.043 mole) and isopropylamine (10.1 grams, 0.17 mole) are mixed and refluxed for 12 hours using an efficient reflux condenser. The mixture is then cooled and poured into 100 ml. of 5% hydrochloric acid and extracted with diethyl ether. The ether extract is dried over magnesium sulfate. Removal of the drying agent and solvent leaves an orange oil which readily solidifies. The product is recrystallized from methanol to give 8.7 grams (80%) of an orange solid with melting point 69° C. to 70° C.

Workup

  1. temperaturerefluxed for 12 hours
  2. temperatureThe mixture is then cooled
  3. additionpoured into 100 ml
  4. extractionof 5% hydrochloric acid and extracted with diethyl ether
  5. extractionThe ether extract
  6. dry with materialis dried over magnesium sulfate
  7. customRemoval of the drying agent and solvent
  8. customleaves an orange oil which
  9. customThe product is recrystallized from methanol

Sources & evidence

ORD record
ord-e885c64d581c4e96b1f98840408c70e3
Source dataset
uspto-grants-1980_10
Patent number
US04227913

Reaction notes

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