1-Chloro-4-nitrobenzene → 4-nitro-N-(tetrahydrofuran-2-ylmethyl)aniline

HRID 26337

Reaction equation

HRID 26337 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([NH2:17])[CH:12]1[O:16][CH2:15][CH2:14][CH2:13]1>O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:17][CH2:11][CH:12]2[O:16][CH2:15][CH2:14][CH2:13]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 74741-Chloro-4-nitrobenzeneHCID 253298Tetrahydrofurfurylamine

Product 1

HCID 226105934-nitro-N-(tetrahydrofuran-2-ylmethyl)aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.3 mol (46.2 g) of para-chloronitrobenzene and 1 mol (101 g) of tetrahydrofurfurylamine are heated for three hours in an oil bath at 150° C. The reaction medium is then poured into 500 ml of ice-cooled water. The expected product initially precipitates in the form of a thick oil which rapidly crystallises. After it has been filtered off, washed with water, recrystallised from ethanol and dried in vacuo, the product melts at 74° C.

Workup

  1. customThe expected product initially precipitates in the form of a thick oil which
  2. customrapidly crystallises
  3. filtrationAfter it has been filtered off
  4. washwashed with water
  5. customrecrystallised from ethanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-8e760d57566e4935a58717f2a533efcf
Source dataset
uspto-grants-1979_04
Patent number
US04149848

Linked notes

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