Methylamine → HCID 20071071, compound

HRID 2291439Notes

Reaction equation

HRID 2291439 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[C:3]=1[N+:10]([O-:12])=[O:11].CN.ClC1C=[C:20]([NH:22]C)C([N+]([O-])=O)=C(NC)C=1>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([NH:22][CH3:20])[C:3]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 292282,4,6-TrichloronitrobenzeneHCID 20071079HCID 20071079, compound

Product 1

HCID 20071071HCID 20071071, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.150 mole (34 g) of 2,4,6-trichloronitrobenzene is added portionwise, at ambient temperature, to 300 ml of a 30% strength solution of methylamine in absolute ethanol. After stirring for 23 hours at ambient temperature, a precipitate, consisting essentially of 4-chloro-2-methylamino-6-methylaminonitrobenzene, is removed by filtration. The filtrate is evaported to dryness under reduced pressure. 800 ml of concentrated hydrochloric acid are added to the dry extract obtained in this manner. The insoluble fraction is removed by filtration. After dilution of the filtrate with 650 ml of water, the expected product precipitates. It is washed with water and is then dried under vacuum in the presence of phosphorus pentoxide. After recrystallization from isopropanol and then from absolute ethanol, it melts at 120° C.

Workup

  1. customis removed by filtration
  2. addition800 ml of concentrated hydrochloric acid are added to the dry
  3. extractionextract
  4. customobtained in this manner
  5. customThe insoluble fraction is removed by filtration
  6. customAfter dilution of the filtrate with 650 ml of water, the expected product precipitates
  7. washIt is washed with water
  8. dry with materialis then dried under vacuum in the presence of phosphorus pentoxide
  9. customAfter recrystallization from isopropanol

Sources & evidence

ORD record
ord-c38195ce70ed44fd8bb62dd21748faff
Source dataset
uspto-grants-1989_01
Patent number
US04797129

Reaction notes

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