Diethylamine → HCID 15751484, compound

HRID 1974622Notes

Reaction equation

HRID 1974622 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[F:12].C(NCC)C.[CH:18]1([NH2:21])[CH2:20][CH2:19]1>O>[Cl:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:7]=1)[NH:21][CH:18]1[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 69828CyclopropylamineHCID 157514831-Chloro-2,5-difluoro-4-nitrobenzene

Product 1

HCID 15751484HCID 15751484, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Chloro-2,5-difluoro-4-nitrobenzene (3.69 g, 19 mmol) is treated at 0° with diethylamine (2.3 g, 23 mmol) and cyclopropylamine (1.3 g, 23 mmol). After 1 hour at 0° the suspension obtained is stirred at 25° for 16 hours. The reaction mixture is taken up in water (150 ml) and extracted with ethyl acetate. The organic phase is washed with 10 percent sodium chloride solution and dried over magnesium sulfate. After distillation of the solvent the residue is recrystallized from ethanol (50 ml). There are obtained 3.5 g (79%) of 5-chloro-N-cyclopropyl-4-fluoro-2-nitroaniline with a m.p. of 73.5°-75.5°.

Workup

  1. customAfter 1 hour at 0° the suspension obtained
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with 10 percent sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. distillationAfter distillation of the solvent the residue
  6. customis recrystallized from ethanol (50 ml)

Sources & evidence

ORD record
ord-2a7adbbb2395403ab212fcc313a3056a
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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