4-Chloro-1,2-dinitrobenzene → HCID 10730655, compound

HRID 2258535Notes

Reaction equation

HRID 2258535 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[N+:11]([O-])=O)([O-:3])=[O:2].[CH:14]1([CH2:20]N)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C(O)C>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([NH:11][CH2:20][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:6]=1

Participants

4

Reactant 2

HCID 330974-Chloro-1,2-dinitrobenzeneHCID 76688Cyclohexanemethylamine

Product 1

HCID 10730655HCID 10730655, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 8.1 g of 1,2-dinitro-4-chlorobenzene in 20 ml of 95% ethanol is added dropwise a solution of 13.6 g of cyclohexylmethylamine in 10 ml of 95% ethanol. The temperature rises to 50° C. The reaction medium is kept stirring for 2 hours and the solvent is then evaporated off under vacuum. The residue is taken up in DCM, washed with water, then with 2N hydrochloric acid and next with water, dried over Na2SO4 and the solvent is then evaporated off under vacuum. The residue is chromatographed on silica, eluting with isopropyl ether. After recrystallization from heptane, 4.21 g of the expected product are obtained, mp=73° C.

Workup

  1. customrises to 50° C
  2. customthe solvent is then evaporated off under vacuum
  3. washwashed with water
  4. dry with materialwith 2N hydrochloric acid and next with water, dried over Na2SO4
  5. customthe solvent is then evaporated off under vacuum
  6. customThe residue is chromatographed on silica
  7. washeluting with isopropyl ether
  8. customAfter recrystallization from heptane, 4.21 g of the expected product
  9. customare obtained

Sources & evidence

ORD record
ord-39719614d4094e66849788f4e86a8580
Source dataset
uspto-grants-1997_08
Patent number
US05661169

Reaction notes

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